Homes for Sale Near Sarasota High in Sarasota - 765 homes

Remarks: One or more photo(s) has been virtually staged. Ideally positioned in Sarasota’s desired West of Trail, this 2012 custom-built three-bedroom, four-bath home blends timeless architecture with modern comfort—just a short stroll to Southside Village’s boutiques and cafés, Selby Gardens, the bay front, and Sarasota Memorial Hospital. Set on a fully fenced, 1/3-acre lot in the sought-after Southside Elementary district, the property offers a private oasis with a sun-soaked southern-exposure backyard—ideal for all-day light on the pool and covered patio. Outdoor living shines with a heated pool featuring a sun shelf, fire pit, landscaped lawn, and inviting front and back porches designed for effortless entertaining. Inside, nearly 2,800 square feet unfolds with a wood-burning fireplace, tile and luxury vinyl plank flooring, and a flexible layout suited for today’s lifestyle including a den/office that can easily be used as a fourth bedroom. The oversized laundry/mudroom streamlines daily life, while the two-car garage with extra storage adds convenience. The spacious primary suite opens directly to the pool and features dual walk-in closets and bath with double vanities, a walk-in shower, and soaking tub. Built with quality in mind—including block construction and a durable metal roof—this home offers peace of mind and enduring value. A rare opportunity to own newer construction West of Trail with accessibility, abundant natural light, and room to live the Sarasota lifestyle to its fullest—just minutes from downtown.

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)

Listing Agent: Katy Mcbrayer (941-400-2406)

Remarks: Welcome to 4160 Fruitville Rd, Unit 11—a beautifully updated residence that balances comfort, convenience, and an easygoing Florida lifestyle. Step inside to find brand-new flooring that brings a fresh, modern feel throughout the living spaces. Natural light draws you toward a serene pond view, offering a daily backdrop of calm and privacy—an increasingly rare feature at this price point. The home features a large primary bedroom, providing ample space for a full bedroom set along with a sitting area or workspace—an inviting retreat at the end of the day. Practical details are just as appealing: the unit includes an assigned covered parking space, adding both convenience and protection from the elements. The community itself is rich with amenities designed for both relaxation and social connection. Residents enjoy access to a sparkling pool and an expansive clubhouse featuring a billiards room, library, fitness center, full kitchen, and saunas—a setting that supports everything from quiet afternoons to lively gatherings. Location is another strong advantage. With close proximity to I-75 and just a short drive to downtown Sarasota, you’re well positioned for commuting, dining, shopping, and the cultural offerings that make the area so desirable. This is a home that offers both ease and livability—well-suited for a primary residence or a seasonal retreat.

Listing is courtesy of: BLUE SKY REAL ESTATE (941-587-3492)

Listing Agent: John Werner (941-587-4579)

Remarks: Price Reduction!! ENJOY AWE-INSPIRING SUNRISES AND SUNSETS from this stunning two bedroom, two bath PENTHOUSE condo at the southernmost end of Siesta Key. A corner unit with extra windows, enjoy water views from every room! Wake to breath-taking sunrises over Neville Preserve on Little Sarasota Bay and marvel at spectacular sunsets over the Gulf of Mexico. The largest of units offered at The Pointe, this 10th floor residence is filled with natural light through abundant windows and sliding glass doors. The large kitchen opens to the living room which features beautiful engineered hardwood flooring, crown and base molding, and ceiling beams to separate the dining and living areas. A generous screened and glassed lanai - accessible from both the living room and the primary suite - provides your front-row seat to sunrises, downtown Sarasota, and spectacular wildlife. The private primary retreat offers a large bedroom, a walk-in closet, a built-in vanity with sink, and an ensuite bath with walk-in shower, second sink and toilet. A comfortable guest bedroom and full hall bath complete the main living space. A large laundry room with ample cabinetry, a walk-in utility room off the lanai and a large ground floor assigned lock-off bin provide coveted storage space. An oversized under-building parking space convenient to the building entry completes this unit. Located at the southern tip of Siesta Key, this 5+ acre gated community is beautifully landscaped and features every amenity: heated pool and spa, lighted tennis and pickle ball courts, private boat docks, kayak and canoe racks and launch, a beautiful and fully equipped club house, saunas, fitness centers, an island pavilion with grills, and on-site management and maintenance. A walkway along the water surrounding the property is idyllic for scenic strolls. The Pointe is just minutes' walk to Turtle Beach and three great restaurants. This really is a must see!

Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)

Listing Agent: Robert Ruiz (941-544-3299)

Remarks: Under contract-accepting backup offers. Don't let this one get away! * LOCATION, LOCATION, LOCATION * Rarely available in the GATED community of The Woodlands of Bent Tree * This EXQUISITE EXECUTIVE FAMILY HOME BOASTS A VERY PRIVATE SETTING ON ALMOST 3/4 ACRE, BACKING TO A WOODED GREENBELT * Quiet cul de sac location which means no through traffic * Side-load OVERSIZED 2 Car Garage * Quality Built by Arthur Rutenberg Homes and IMPECCABLY MAINTAINED BY THE ORIGINAL OWNERS, you will not find a home with this QUALITY & PRIDE OF OWNERSHIP * 4 Bedrooms & 3 Full Baths * 2 Bedrooms are En-suites * Formal Living Room & Formal Dining Room * The THOUGHTFULLY REIMAGINED Chef's Kitchen is open to the Family Room with a Wood-burning Fireplace * The generously-sized Owners' Suite showcases a Spa-style Bath with Walk-in Closet, Dual Sinks, Shower and a Garden Tub * All of this wraps your PRIVATE OUTDOOR OASIS with a CAGED POOL & SPACIOUS COVERED LANAI * This is the perfect home to entertain family & friends or for just relaxing in your slice of paradise * 'A' RATED SCHOOL DISTRICT * Short 15 minute drive to World Famous Siesta Key Beach as well as UTC Mall * You are close to all of Sarasota's fabulous amenities * One look & you'll fall in love! *

Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)

Listing Agent: Ryan Brown (941-330-7774)

Remarks: Under contract-accepting backup offers. This is the one * QUALITY BUILT BY LEE WETHERINGTON HOMES * LOCATED BEHIND THE GATES OF RARELY AVAILABLE TUSCANA WHERE YOUR DREAM HOME AWAITS * 'A' RATED SCHOOL DISTRICT * Lovingly cared for by the original owners and the PRIDE OF OWNERSHIP SHOWS * This IMMACULATE home will not disappoint * This Family Estate Home is located on a Premium Lot backing to a 10 Acre Preserve & Pond providing a natural oasis & sense of tranquility * Enjoy the INCREDIBLE SUNSETS * This Custom Built Casablanca model is meticulously designed with 4 Bedrooms that are ALL EN-SUITES + 5 FULL BATHS + a Private Den/Office * The heart of the house is undoubtedly the LOVINGLY RENOVATED CHEF'S KITCHEN with NEW QUARTZITE Countertops, Upgraded Monogram Appliances, Custom Wood Cabinets, NATURAL GAS COOK-TOP, Built-in Oven, an Oversized Refrigerator & a Walk-in Pantry * The Gourmet Kitchen is open to the SPACIOUS FAMILY ROOM * Formal Living Room & Formal Dining Room * The Primary Suite is a sanctuary of comfort and a true retreat that features a THOUGHTFULLY REIMAGINED Spa-style Bath with NEW Walk-in Shower, Freestanding Tub, Dual Vanities & Dual Walk-in Closets * Upstairs is perfect for Guests or a private getaway with 2 En-Suite Bedrooms & a 23 x 17 Bonus Room with a Wet Bar, Mini Refrigerator, Ice Maker & Microwave * Relax on your 2nd story Screened Veranda - THE VIEWS ARE INCREDIBLE! * All of this wraps your Outdoor Oasis with Double Lanais * The Main Lanai is 21x16 with a Built-in Kitchen and a GAS Fireplace * Welcome to Party Central with a Beer Keg Built-in, Mini Refrigerator, Sink, GAS Grill & a Built-in Exhaust System * Travertine Deck * Your SALTWATER Pool & Spa is GAS Heated with a beach style shelf PLUS an Extended Paver Deck outside of the Pool Cage for additional enjoyment * You will not find a better outdoor area than this * Very Private Setting backing to tranquil 10 Acre Preserve & Pond to enjoy the spectacular sunsets * This is the perfect home for entertaining friends & family or simply relaxing in your slice of paradise * 3 Car Garage * NATURAL GAS * Volume Ceilings * Crown Molding * Tray Ceilings * Well for Yard Irrigation * Beautiful Landscaping + Paver Driveway + Sidewalks * Friendly GATED Neighborhood of only 99 Homes * NO CDD Fees * Located in the heart of Sarasota and close to shopping, dining, golf courses & more! * A short drive to World Famous Siesta Key Beach as well as UTC Mall * This truly outstanding home is a MUST SEE * Furniture is available under separate negotiation * One look & youll fall in love * Run, don't walk! *

Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)

Listing Agent: Ryan Brown (941-330-7774)

Remarks: Welcome to this versatile Sarasota gem offering space, flexibility, and freedom. Situated on an oversized lot, this 4-bedroom, 2-bath home includes a well-appointed mother-in-law suite featuring 2 bedrooms, a full kitchen, a full bathroom, and a private entrance. The layout allows the home to be used as two separate living units or kept open for a larger or multi-generational family. This home has seen several recent updates, including a new roof installed in January 2025 with warranty, new vinyl flooring throughout in 2025, and air conditioning systems serviced in July 2025 for added peace of mind. A new submersible pump installed in February 2024 comes with a warranty through 2027. A new septic system was installed in 2021. The relaxed, laid-back neighborhood has no HOA, giving you the freedom to park your RV, boat, or other toys right at home. The oversized lot offers ample outdoor space with room to expand, entertain, or store equipment. Ideally located close to shopping, major highways, and just minutes from downtown Sarasota, this property also offers easy access to the area’s world-famous beaches. Whether you’re seeking a primary residence, multi-generational living, or income-producing potential, this home delivers outstanding value in a prime Sarasota location. 2 of the bedrooms and the 2nd kitchen are not reflected on the appraiser's website and public records, Information deemed reliable but not guaranteed. Buyer to verify all information. Don't wait call for your showing today!

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Brandon Graber (941-330-3808)

Remarks: This stunning one-story custom-built home, completed in 2020, offers the ideal blend of modern design, high-quality construction and an unbeatable location. In the sought-after Southside Elementary School district, this three-bedroom, three-bath residence plus dedicated office is just minutes from Siesta Key, downtown Sarasota and Sarasota Memorial Hospital, placing you at the heart of everything that makes Sarasota exceptional. Designed for comfort and style, this home features a seamless open floor plan with soaring ceilings, corner pocket doors in the office and abundant natural light. The spacious kitchen is a chef’s dream, boasting quartz countertops, an oversized island, custom cabinetry and top-tier appliances. The smoky mirror wall at the entryway and built-in bookshelves add unique character, while recessed LED lighting enhances the contemporary ambiance. Go outside through the expansive sliding glass doors to your private backyard retreat. The pool and spa are surrounded by lush traveler palms, creating a serene, tropical escape. The fully fenced-in yard and generous patio space make this the ideal setting for entertaining or unwinding in privacy. Additional highlights include solid block construction, hurricane/impact-rated windows and doors, a two-car garage with additional driveway parking and a paver driveway for an elegant touch. With no HOA or CDD fees, this move-in-ready home offers the rare opportunity to experience luxury living in one of Sarasota’s desirable neighborhoods. Schedule your private tour today!

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)

Listing Agent: Katy Mcbrayer (941-400-2406)

Remarks: Live the Downtown Waterfront Lifestyle – Deeded Dock Included! Brand new exterior paint! This beautifully renovated 2-bed, 2-bath condo with a den (optional 3rd bedroom) is a rare find in Sarasota’s desirable West of the Trail neighborhood. Located in Hudson Landings, a quiet 12-residence community just minutes from downtown and the bay, this light-filled second-floor corner unit offers modern updates and an unbeatable lifestyle. The list price includes a deeded dock and a 10,000-lb boat lift—brand new with updated pilings and cradle—providing quick, direct access to Sarasota Bay and the Gulf of Mexico. Bring your boat and enjoy the ultimate Florida living experience! Inside, you'll find a vaulted exposed-beam ceilings and abundant natural light with a sleek contemporary kitchen with custom cabinetry, newer granite countertops, glass tile backsplash, and top-of-the-line stainless steel appliances, including a built-in double oven and glass cooktop, and a spacious Italian-style shower in the updated bathrooms. Plus a cozy wood-burning fireplace for cool evenings and an enclosed patio with large hurricane-rated sliding windows, creating a bright and inviting dining area Step outside and you’re just a short walk to Marie Selby Botanical Gardens, the Sarasota Bayfront, and vibrant downtown Sarasota. This peaceful community also features a heated pool, lush landscaping, and a truly secluded atmosphere—no damage from recent storms Helene or Milton; docks and boats remained intact.

Listing is courtesy of: YORKSHIRE INTERNATIONAL R.E. (941-366-0000)

Listing Agent: Jules Roman (941-366-0000)

Remarks: Welcome to this beautifully updated 3-bedroom, 2-bathroom home in the highly sought-after South Gate neighborhood of Sarasota, ideally located just minutes from world-famous Siesta Key Beach and vibrant Downtown Sarasota. Situated on a highly desirable corner lot, this move-in ready home offers exceptional curb appeal with a newly installed 8-ft vinyl fence, along with a new roof, fascia, and gutters completed in 2023. Step inside to an inviting, light-filled living space where large windows create a bright and airy atmosphere. The flexible layout flows seamlessly into a versatile bonus area—perfect for a home office, sitting room, or additional entertaining space. The updated eat-in kitchen is the heart of the home, featuring freshly painted cabinetry, quartz countertops, stainless steel appliances, and a stylish backsplash—designed for both everyday living and hosting. A dedicated laundry room with built-in shelving doubles as a convenient pantry for added storage, and the home includes a new washer and dryer. French doors lead to the screened lanai, with upgraded wood tile flooring, creating a warm and inviting outdoor living space perfect for relaxing or entertaining. The fully fenced yard, mature canopy, and producing lychee tree contribute to a setting that feels both established and quietly distinctive. This backyard also offers room for play and possibly a pool for the future owner. The primary suite offers a peaceful retreat with an updated ensuite bathroom, featuring a new vanity and walk-in shower. Additional upgrades include fresh interior and exterior paint, new landscaping, vinyl flooring throughout, and added attic insulation (2024) for improved energy efficiency. This home is equipped with hurricane shutters, a 360-degree security system, and surge protection in the electrical panel for added protection and peace of mind. Furniture is available for purchase separately, making this a potential turnkey opportunity. Residents have the option to join the voluntary HOA, which provides access to the South Gate Community Association pool—an added perk that enhances the neighborhood lifestyle. Enjoy an unbeatable Sarasota lifestyle just minutes from shopping, dining, and entertainment, with easy access to the Legacy Trail, Siesta Key and St. Armands Circle. Whether you're searching for a primary residence, seasonal retreat, or investment property, this South Gate home offers the perfect blend of location, upgrades, and lifestyle. The property is maintained with consistent professional care, supporting long-term integrity. Schedule your private viewing today!

Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)

Listing Agent: Roni-Marie Gold, Pa (941-487-0105)

Remarks: Welcome home to this beautiful 3-bedroom, 2-bath villa with a 2-car garage, located behind the gates of Bent Tree Village in Hammocks 1. This split-bedroom floor plan offers both space and privacy, with formal living and dining areas, vaulted beam ceilings, and a separate Florida room featuring new hurricane-rated skylights. From there, enjoy views of the open-air patio and peaceful trees beyond. The newly renovated 2025 kitchen features quartz countertops, all-new cabinetry, pull-out lower drawers, and newer stainless steel appliances. The laundry closet is conveniently located in the kitchen. The oversized primary suite includes an ensuite bath with dual vanities, a walk-in shower, and a large walk-in closet. On the opposite side of the home, you’ll find two guest bedrooms and a full guest bath. This villa is located in Hammocks 1, which is not a 55+ community. You’ll also love the convenient location near I-75, restaurants, shopping, and just a short drive to the area’s beautiful beaches or UTC Mall. Don’t miss your chance to make this lovely villa your new home.

Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)

Listing Agent: Lisa Bouck, Pa (941-374-0165)

Remarks: Looking for a home for your boat, a beach lifestyle, or an investment? Enjoy sunrises over the marina, afternoons on Siesta Key Beach, and evenings on your enclosed balcony overlooking the boats and colorful skies. This furnished 1BR/2BA condo in Siesta Harbor is beautifully updated with an open floor plan, luxury vinyl flooring, remodeled kitchen (2022) with white shaker cabinetry, granite counters, glass backsplash, peninsula seating, and stainless appliances. Bathrooms feature quartz vanities and tiled showers; guest bath includes a soaking tub. Impact windows, same-floor laundry, and private storage add convenience. Siesta Harbor, a 55+ community, offers private beach access, heated pool/spa, lush landscaping, fishing pier, and a full calendar of social activities. Dock leases may be available for boats up to 30’. Additional amenities include covered parking, on-site manager, and a new roof (2025). Ideally located off the South Bridge near dining, shops, and the free Siesta Key trolley, this turnkey condo is perfect as a vacation retreat, full-time residence, or investment.

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

Listing Agent: Marci Mcfarland (941-961-3390)

Remarks: Siesta Royale is a Beachfront complex on Siesta Key located on the world famous Crescent Beach. This unit is Located right by the pool and close to the beach. This unit has been updated with High end laminant flooring throughout, new appiances, Granite counters and all new impact windows with beautiful finishing touches that makes you feel like you are really on vacation. Perfect for investment or full time use, Parking right outside unit, No stairs. This complex is close to many retaurants, boating, parasailng and shopping. This unit has a good rental histoy with steady rentals though out the year. Dont miss this one.

Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)

Listing Agent: Tom Ward (941-350-2463)

Remarks: Under contract-accepting backup offers. Luxury Waterfront Living Spectacular Views, Resort-Style Amenities Wake to breathtaking sunrises over Little Sarasota Bay and the Intracoastal Waterway. This fully remodeled and furnished 2-bedroom, 2-bath condo offers 1,093 square feet of refined coastal living where the views are the true centerpiece. The Residence Thoughtfully renovated in 2024, this residence blends the modern finishes with timeless coastal elegance. The open living and dining areas are bathed in natural light and perfectly positioned to capture sweeping water views, creating an inviting space for both everyday living and entertaining. Features include: 2 Bedrooms, 2 Bathrooms 1,093 Square Feet Panoramic Bay & Intracoastal Views Luxury Vinyl Flooring (2024) New Stainless-Steel Appliances (2024) New Hot Water Heater (2024) New A/C System (2025) Quartz Countertops Offered Fully Furnished with Upscale Furnishings & Accessories Move-In Ready Resort-Style Waterfront Community Enjoy an amenity-rich lifestyle designed for relaxation, wellness, and recreation: Tennis & Pickleball Courts Two Heated Pools-Including an Olympic-Size Pool with Lap Lanes Clubhouse with Pool Table and Ping Pong Fitness Center with Weight & Exercise Equipment Boat Docks Available for Lease Waterfront Setting with Direct Intracoastal Access An Unmatched Coastal Location Turtle Beach directly across the road Shuttle stop providing easy access to Siesta Beach and Siesta Village World-class beaches, boating, dining, and shopping just minutes away The Lifestyle This home is all about the views- sparkling water, passing boats, and unforgettable sunrises enjoyed from the comfort of your living space. Whether as a primary residence, seasonal retreat, or investment property, this condo delivers a luxury waterfront lifestyle with effortless ease.

Listing is courtesy of: PETER D DONAHUE LICENSED REAL ESTATE BROKER (239-206-0740)

Listing Agent: Peter Donahue (239-206-0740)

Remarks: A striking triumph of modern architecture and engineering, this three-story contemporary estate in Harbor Acres—Sarasota’s most coveted neighborhood—stands as a bold statement of design, innovation, and uncompromising luxury. Designed by renowned architect Mark Sultana of DSDG Associates, the residence is a masterwork where precision and artistry converge. From the moment of entry, soaring ceilings, expansive walls of glass, and a dramatic Italian floating staircase set the tone. Natural light fills the interiors, enhancing a layout designed for both impact and livability. The main level is anchored by an open-concept great room and a chef’s kitchen of exceptional caliber. A full suite of Miele appliances—including induction cooktop, built-in espresso maker, warming drawers, dual microwaves, and a full-height wine tower—is paired with Dekton countertops and custom Westwood cabinetry. A concealed butler’s pantry with Sub-Zero refrigeration enhances functionality. Living and dining areas flow seamlessly to a covered terrace with a summer kitchen and thermally modified wood ceiling overlooking the private grounds. The north wing is dedicated to a dual-owner’s suite—two private retreats connected by a spa bath with floating vanities, dual rain showers, soaking tub, heated towel racks, and custom Italian closets. One suite is currently configured as a refined office. The second living level offers a library/media room that can convert to a two-room guest suite, an additional bedroom suite, and two full baths for comfort and privacy. Outdoors, a resort-style setting unfolds with a dramatic 50-foot heated pool and spa, covered lounge areas, and lush bamboo for privacy. A separate one-bedroom guest house with full bath, coffee bar, and mini refrigerator provides independent accommodations. The rooftop terrace captures sweeping panoramic views of Sarasota Bay, the Ringling Bridge, Longboat Key, Siesta Key, and the downtown skyline—an exceptional setting for sunset gatherings. Additional features include Crestron-controlled lighting, shades, and audio, integrated speakers, five Luma security cameras with remote access, and two climate-controlled garages for up to six vehicles with epoxy floors, storage, and a gym opening to the pool terrace. A rare architectural statement offering elevated design, privacy, and location just minutes from downtown Sarasota and the Bayfront.

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

Listing Agent: Kim Ogilvie (941-951-6660)

Remarks: Welcome to 1313 Siesta Bayside Drive in Gulf & Bay Club Bayside, a beautifully updated 2-bedroom, 1.5-bath condo offered turnkey furnished and ideally suited as a personal beach retreat or high-performing investment property with weekly rental flexibility and consistent future bookings already in place. This light-filled residence features tasteful coastal updates and a serene pond waterview, complemented by a private single-car garage, driveway parking, and additional guest parking conveniently located across the street. Enjoy deeded beach access to world-famous Siesta Beach, renowned for its bright white quartz sand and crystal-blue Gulf waters, just a short walk away, while the Siesta Key Village shops and restaurants are an easy drive, bike, or golf cart ride. Gulf & Bay Club Bayside is a gated, resort-style community offering two heated pools, tennis and pickleball courts, walking paths, a fishing pier, fitness center, clubhouse, BBQ and picnic areas, and lush tropical landscaping, delivering the perfect blend of relaxed island living and strong income potential in one of Siesta Key?s most desirable communities.

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

Listing Agent: Shane Lewis (941-685-3252)

Remarks: One or more photo(s) has been virtually staged. Tucked beneath a canopy of mature trees in one of Sarasota’s most coveted neighborhoods, 1714 South Drive presents a rare opportunity to secure a prime homesite in Cherokee Park, West of the Trail and moments from the very best of Sarasota living. Set on a beautifully established lot with lush, mature landscaping, a paver driveway, and a combination of garage and carport parking, the property offers an immediate sense of privacy and presence. Inside, the home unfolds with a surprisingly expansive footprint and a floor plan that captures natural light throughout. A welcoming entry with a leaded stained-glass door opens to multiple living spaces, including a living room with a wood-burning fireplace, custom built-ins, and distinctive Saltillo tile flooring, alongside a light-filled family room wrapped in windows with views of the pool and direct access to the lanai. The dining room, positioned with a bay window overlooking the pool, connects seamlessly to the kitchen, which features granite countertops, glass-front cabinetry, a center island with cooktop, and a breakfast nook with access to a private side deck. The layout offers flexibility with multiple bedroom and office options, including a front bedroom or office with a wall of windows and an in-wall safe, and a private guest suite with its own bath showcasing vintage turquoise tile and retro detailing. A secondary guest bedroom includes built-in workspaces and shelving, ideal for dual office use or creative space. The primary suite is tucked privately toward the rear of the home, offering direct access to the lanai, abundant natural light, and a spacious bath with dual vanities, soaking tub, walk-in shower, and skylight above. Additional spaces include a bonus room off the garage with bedroom conversion potential, a pool bath, and a separate flex space off the lanai with wood-paneled walls and its own mini-split system, ideal for a studio, gym, or additional lounge. Outdoors, the home continues to deliver with an oversized, caged pool and covered lounging areas, surrounded by mature landscaping, stone walkways, and a fully fenced yard. An existing outdoor kitchen structure and multiple access points from the home create a true indoor-outdoor flow that aligns perfectly with Sarasota’s year-round lifestyle. What truly elevates this property is its location. Just moments from the shops and restaurants of Southside Village or downtown Sarasota’s waterfront, cultural venues, and marina. It is close to Sarasota Bay and just a short drive to Siesta Key’s north bridge. This is a setting that defines convenience and coastal luxury. Cherokee Park remains one of the most desirable addresses in Sarasota, and 1714 South Drive offers the rare combination of location, lot, and layout, an exceptional opportunity in the heart of Sarasota.

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

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

Remarks: Under contract-accepting backup offers. Tucked behind a gate on a quiet, private road in one of Sarasota’s most sought-after neighborhoods, this is the kind of property families wait years for—where space, privacy, and lifestyle all come together just minutes from everything. Located West of Trail, just blocks from Southside Elementary and Southside Village, and a short drive to downtown Sarasota and Siesta Key Beach, this estate offers a rare balance: a secure, expansive family compound in the heart of it all. Set on over half an acre and fully gated, fenced, and lushly landscaped, the property is designed for those who want room to live, grow, and entertain privately—without sacrificing convenience. The main residence spans nearly 4,000 square feet with 5 bedrooms, 4 full bathrooms, 2 half baths, a private office, and a large game room or playroom with its own wet bar—perfect for families who need flexibility in how they live day-to-day. Whether it’s a dedicated workspace, kids’ zone, or media room, the layout adapts to your lifestyle. The kitchen is built for real life and entertaining alike, featuring Viking appliances, generous storage, and an open flow into the main living areas and outdoor spaces. Every bedroom includes an ensuite bath, offering comfort and privacy for family and guests. Step outside and the home truly opens up. A large covered lanai with outdoor kitchen overlooks the heated, self-sanitizing saltwater pool and spa, with a sunken firepit seating area creating a natural gathering space for evenings with friends or family. A dedicated pool bath adds convenience, while the entire outdoor experience is designed for year-round Florida living. For those who need more than just bedrooms, the detached guest apartment above the garage provides over 700 square feet of private living space—ideal for multi-generational living, a nanny suite, long-term guests, a studio, or a secluded home office. And for the car enthusiast or collector, this property stands apart. With 5+ climate-controlled garage spaces—including room for lifts—plus a large all-season carport with motorized louvers, you have the flexibility to showcase, protect, and enjoy your collection. The garages are outfitted with SwissTrax flooring, vacuum systems, and Mitsubishi in-wall AC units—built with intention, not as an afterthought. Beyond comfort and design, the home is equipped for peace of mind. Impact windows and doors, a full CCTV security system, smart home integration, and a Generac generator ensure both safety and ease of living. This is a home for a family who wants it all—space to spread out, privacy to feel secure, proximity to top schools and amenities, and the ability to live an active Sarasota lifestyle, whether that’s golf cart rides to dinner, beach days on Siesta Key, or quiet evenings at home. Because homes that check every box like this—location, land, layout, and lifestyle—are rare. And when they come up, they don’t last.

Listing is courtesy of: EXP REALTY LLC (800-486-1794)

Listing Agent: Mark Coppens (941-444-0436)

Remarks: Pre-Construction. To be built. Discover an extraordinary opportunity to own an expansive double lot of 0.52 acres on North Siesta Key with this single-story, new construction transitional modern-style luxury home by Pham Development. Offering 170 feet of deep-water canal frontage, the residence features 4,353 square feet under air and 15,453 square feet under roof. With 5 bedrooms, 5 full bathrooms, 2 half baths, and a designated private office, the home showcases soaring 17.5-foot vaulted ceilings and a striking glass wine wall, complemented by designer finishes that fill the interiors with natural light and tranquil water views. Across the canal, lush landscaping provides a serene and private backdrop, with flexibility to customize finishes and style. Designed for both comfort and entertaining, the open-concept living spaces flow seamlessly to a resort-style outdoor retreat. The expansive back patio is equipped with remote-controlled electric mosquito screens, allowing you to enclose the space at the touch of a button for year-round enjoyment. Enjoy a spectacular pool with a champagne hot tub spa, a generous patio, and a fully equipped outdoor kitchen perfect for alfresco dining. A scenic path leads to your private dock with a state-of-the-art electric system and space for a boat up to 37 feet, offering smooth access to the bay and Gulf. The primary suite is a private sanctuary with spa-inspired amenities and dedicated quarters. A chef’s kitchen anchors the heart of the home with premium appliances and refined finishes. An elegant circular driveway creates a grand entrance, while the expansive ground level offers room for up to 10 cars, complemented by an impressive 10-car garage—ideal for collectors or additional storage. This exceptional waterfront residence delivers effortless luxury and refined coastal living.

Listing is courtesy of: PHAM REALTY GROUP LLC (941-260-0709)

Listing Agent: Faith Stutzman (941-260-0709)

Remarks: Under contract-accepting backup offers. Pre-Construction. To be built. Pre-Construction. To be built. IMAGINE a Custom Coastal Contemporary Home on Palm Island, Siesta Key. Picture a thoughtfully designed residence offering 2,750 sf of indoor living space and 3,467 sf of total indoor/outdoor space. E/M Custom Homes is renowned for their impeccable craftsmanship and modern coastal design creating a one-of-a-kind residence to be tailored to your lifestyle. This stunning 4-bedroom, 3.5-bath home includes an open Concept Floor Plan, Gourmet Kitchen with custom cabinetry, luxury appliances, and a walk-in pantry—ideal for entertaining. Enjoy a First-Floor Master Suite with a spa-inspired en suite bath and a large walk-in closet. The Second Floor boasts 3 bedrooms, a second gathering room, an office, a laundry room, and a Balcony to relax and enjoy island breezes and views. Be inspired to grill in your Outdoor Kitchen on the expansive covered lanai, perfect for alfresco dining. Lounge in your Custom Designed Private Pool, appreciating outdoor living. You also have an Oversized 2-Car Garage with easy access to the downstairs Laundry/Mudroom entry. Set on 2 lots, totaling 0.45 acres (19,456 sf), this property offers a rare combination of space and luxury. Just a 2 block stroll to sink your toes into the luxurious quartz sand and sparkling water of our award-winning Siesta Key Beach. The Village is minutes away where you will find fabulous restaurants, live music, specialty shops, night life, Sunday Farmers Market, art festivals and more. Your dream coastal lifestyle awaits!

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

Listing Agent: Linda Scheller, Llc (941-806-7981)

Remarks: Positioned directly on the sands of world-famous Siesta Key, this 2-bedroom, 2-bath en-suite condominium offers the perfect blend of personal getaway and income-producing investment. Fully furnished and thoughtfully configured for vacation living, this residence is already an active vacation rental with proven historical returns, making it an ideal opportunity for buyers seeking a property that can help offset ownership costs while providing their own beachfront retreat. Inside, tile flooring throughout creates an easy-care coastal interior designed for high-traffic vacation use, while the split layout with two en-suite bedrooms provides privacy and comfort for guests. A large storage closet dedicated to beach gear and recreational “toys” makes it simple to keep everything needed for effortless days on the sand. From the residence, enjoy views of the Gulf of Mexico and the convenience of direct walk-out access to Siesta Key’s powdery white beach, where beach chairs are available for guests, perfect for owners and vacation renters alike. The location places you in one of the most desirable areas of the island, within walking distance to nearby restaurants, shops, and local favorites, or simply hop on the Siesta Key trolley for easy access up and down the island. With its prime beachfront setting, turnkey furnishings, and established rental performance, this property presents a compelling opportunity to own a slice of Siesta Key that can generate income while serving as your personal coastal escape.

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

Listing Agent: Ryndie Brusco (941-809-6913)