Homes for Sale Near Sarasota High in Sarasota - 726 homes

Remarks: This exquisite new-construction modern residence by Milano Homes, situated on an expansive double lot in the heart of Sarasota, blends elegance, convenience, and investment opportunity. Located within Sarasota city limits, this property qualifies for weekly rentals in one of the area’s most in-demand markets—a highly desirable option that allows for strong income in $160K to $180K range annually. This single-story home offers the ultimate in comfort with no stairs to navigate, featuring four spacious bedrooms, three-and-a-half designer bathrooms, and a two-car garage. The outdoor living space is a private sanctuary, complete with a sparkling pool and spa, outdoor shower, and a large fenced yard ideal for both relaxation and entertaining. As with all Milano Homes, the interiors showcase exceptional craftsmanship and imported Italian finishes. From the state-of-the-art kitchen—equipped with Subzero refrigeration, a Wolf induction cooktop, and Wolf oven—to the custom Italian cabinetry, fixtures, and flooring, every detail exudes sophistication. The open-concept living area flows seamlessly into the outdoor retreat, creating the perfect setting for gatherings and indoor-outdoor living. Perfectly positioned, this property offers easy access to the newly extended Legacy Trail, making it a haven for bikers, runners, and nature lovers. Downtown Sarasota’s vibrant arts, dining, and marina scene is just minutes away, while Siesta Key’s award-winning beaches and St. Armands Circle’s luxury shopping and dining are only a five-minute drive. Whether you’re seeking a full-time residence, seasonal retreat, or an income-producing short-term rental, this home offers an unmatched opportunity to enjoy and invest in the Sarasota lifestyle. Work hand-in-hand with the dedicated Milano Homes professionals to personalize this custom residence, creating a one-of-a-kind dream home tailored just for you.

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

Listing Agent: Rinat Sikdar (941-993-9292)

Remarks: This spacious condo has easy access to Siesta Key Beach and a DEEDED 25-FOOT BOAT SLIP WITH A LIFT!! There is water and electric to the slip (#38). Yes, this is a rare opportunity to have both your boat and a nearby world-famous beach in a nicely laid out two-bedroom, two-bath turnkey furnished condo. The master bedroom has views of the harbor while the guest room has a peaceful garden view. This condo features tile flooring throughout with both HVAC and appliances that are only a couple of years old. The roof was replaced in November 2021, and the unit has a one-car garage with storage above as well as a dedicated parking space in front. In addition, this unit has one of the few private outdoor decks in the community. Harbour Towne offers fantastic amenities, including a clubhouse, heated pool, spa, and tennis/pickleball courts. Enjoy the village by day or evening for great dining, shopping and live music. A complimentary trolley runs by the complex on a regular schedule in season. This is a great place to live and play! Look no further, this is where your fun-filled life begins.

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

Listing Agent: Mina Johnson (941-404-9347)

Remarks: Exceptional Living in Sarasota's Premier Southside Village. Discover quality living in one of Sarasota's most sought-after addresses. This beautifully maintained 3-bedroom, 2.5-bathroom residence offers an excellent combination of thoughtful design, premium finishes, and an enviable location just half a block from the vibrant shops and restaurants of Southside Village. The heart of this home is a spacious great room with soaring 18-foot ceiling and tasteful hand-hewn hardwood oak flooring that exudes warmth and character. A convenient dry bar equipped with its own refrigerator, wine cooler, and adjacent powder room makes entertaining effortless. Integrated surround sound creates the perfect ambiance throughout the first floor, while French doors open to a generous 20' x 12' screened lanai featuring a private relaxing hot tub. The thoughtfully designed kitchen is well suited for the culinary enthusiast, featuring an abundance of custom cabinetry with pull-out shelves, under-cabinet lighting, and expansive counter space. Premium appliances include an island-mounted DCS gas range with professional-grade hood, Sub-Zero refrigerator, Bosch dishwasher, and a built-in Miele espresso/cappuccino maker for your morning ritual. The adjacent dining area provides ample space for gathering family and friends around the table. A downstairs office showcases custom-built cabinetry and shelving, creating an ideal work-from-home environment. Quality touches throughout include solid wood core doors and a convenient in-wall vacuum system. Retreat to your spacious primary bedroom where French doors open to a private balcony overlooking mature, lush landscaping. Dual walk-in closets feature organized closet systems, while the spa-inspired en-suite bath boasts stone countertops, a solid wood vanity with dual sinks, an oversized shower with rainfall sunflower head, and a stunning Oceania jacuzzi soaking tub. Two spacious secondary bedrooms share a Jack and Jill bathroom perfect for family or guests. The upstairs laundry room is thoughtfully equipped with its own sink, folding table, and storage cabinetry. A fully equipped outdoor kitchen and patio bar complete with refrigerator, sink, gas grill w/range hood, kegerator, and granite bar provide a great gathering spot. Hurricane impact windows throughout, a metal roof, and resilient Hardie board siding provide exceptional protection against Florida's elements. Situated 20+ feet above base flood elevation, flood insurance is not required, offering both security and long-term savings. 3-car carport. In addition to the amenities of Southside Village you're in close proximity to Sarasota Memorial Hospital, downtown Sarasota, top-rated schools including Sarasota High and Southside Elementary and only 5 miles to world-renowned Siesta Key beach Everything you love about Sarasota living is moments away. This exceptional residence offers the complete package: prime location, superior construction, thoughtful amenities, and the ultimate Sarasota lifestyle. Schedule your private showing today. ________________________________________

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

Listing Agent: Allen Conrad (941-544-0143)

Remarks: Don’t miss this adorable SOUTHSIDE ELEMENTARY-zoned gem in hip South Gate! The location could not be more convenient – walk to the Crossings at Siesta Key Mall and less than a mile to the north bridge to Siesta Key itself! For those with school-age children, the close proximity to Brookside Middle School and Southside Elementary zoning are great perks. Completely updated inside with an elegant kitchen (granite, pretty backsplash, stainless appliances), chic wood-look flooring throughout, a charming fireplace, and recently renovated baths, it is move-in ready! Ideally positioned for ultimate convenience to the many amenities of Sarasota, with wonderful possibilities from a full-time or seasonal abode to a prime investment opportunity. The space inside is used really well, with nice spacious bedrooms and a split-bedroom plan, and outside you’ll enjoy a covered screened patio and HUGE fully fenced backyard! There is currently a fun fire pit and open land, so the large yard can be a blank canvas for your outdoor Florida dreams. There is plenty of space for a pool, if that is your desire, or maybe you prefer to plant an edible garden? The choice is yours and this lot can accommodate it all! An oversized 1-car garage with separated extra storage space and laundry completes the package. Easy to show, schedule your visit today!

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

Listing Agent: Allison Werner (941-961-3212)

Remarks: Under contract-accepting backup offers. BACK UNDER CONTRACT. BACKUPS WELCOMED. Lovely spacious home on quiet premium oversized cul-de-sac parcel with 180-DEGREE WATER VIEW AND NOT IN A FLOOD ZONE! Enjoy sunsets from your lanai every night and the peace of mind knowing there is a BRAND NEW 2025 TILE ROOF overhead... Freshly painted interior; Immaculately maintained; New Luxury Vinyl Wood Flooring in all 1st floor public areas; FIRST FLOOR PRIMARY ENSUITE BEDROOM AND SITTING AREA with a lovingly upgraded DUAL VANITY bathroom; Natural gas; Upgraded 18 +/- month old Kitchen Appliances; Two 2019 Air Conditioners; 18 foot Ceilings in Family room and Kitchen; Split, Open Floorplan; 10 foot Ceilings in Primary Ensuite; Access to lanai, saltwater pool and water view from multiple first floor locations; Flexible floor plan ... On the First Floor: Primary Ensuite Bedroom and either 5th bedroom with full bath OR Office/Den plus Pool Bath; Upstairs 3 Bedrooms and 2 Baths (1 Ensuite); In Excellent School District and near multiple private schools; Freshly Resealed Paver Driveway, Front Walkway and Pool Deck; 3 Car Garage Salt Water, Heated Swimming Pool with 180 degree water views and generous lanai area for luxuriating outdoors; Hurricane Sutters for all openings; Irrigation System with Reclaimed Water; Wonderful MOVE-IN-READY in super convenient location ...LOW HOA FEES ... NO CDD ... Lovely Community Amenities which include: Clubhouse, Fitness Center, Pickleball Courts and Community Pool. Easy to show ... GATE CODE REQUIRED FOR SHOWINGS; Seller downsizing and moving to another Florida city. A GREAT BUY for some lucky person.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)

Listing Agent: Anne Mitchell (941-725-0227)

Remarks: RARELY AVAILABLE AT THIS NEW PRICE!! SHADOW OAKS ESTATES 4 BEDROOM POOL HOME! JOB TRANSFER, SELLER MOTIVATED! Over 2600 Sq/ ft under Newer Roof (2024). Custom Built home on Cul-de-sac in this small Neighborhood near Celery Fields Park, new Concert & Music Hall, new County Administrations buildings, Library & History center expansion, not to mention New Shopping & Restaurants off Fruitville Road! Be in the middle of it all, yet quietly on the Edge! 4 Bedroom 2 story home, with Primary Bedroom on the First Floor. Tile & Wood Flooring throughout the main level. Completely Remodeled & improved Kitchen, Bathrooms & primary Bedroom. Cul-de-sac location with Pond in the middle. 3 Car Garage with Paver Driveway & Walkway to Front Door, Stone accents on front facade makes for lovely Curb appeal. First floor has Living room, Tiled floors, Formal Dining room, Wood flooring, Tray ceiling, Bay Window & Banquette with extra Storage. Beautiful Quartz counters, updated Cabinets with Glass accents, Subway Tile Backsplash, custom Lighting, & built-in desk. New Appliances include Samsung Glass front Range & Refrigerator. First floor Primary bedroom with Wood floors, Dual Walk-in Closets, En-suite bathroom. Separate Tub & Walk-in Shower, Vanity & Dual sinks. Upstairs, a Balcony takes you left to 2nd Bedroom, or Office, secluded from the other 2 bedrooms. Go right to 3rd Bedroom & 2nd bath. Large Bonus or 4th Bedroom over garage. Window seat in dormer flanked by 2 Closets. 2nd Dormer with 6x10 Alcove with window. All 3 bedrooms upstairs are Spacious. Paver Lanai, Caged & Covered space for Seating on either end of Salt water pool. Laundry room, washer & dryer remain. Pre-wired for Central Vac, Security system, Plumbed & wired for Pool Heater plus a Concrete slab for it. Plywood Hurricane shutters & First floor Generator powered by Propane makes this storm ready. Almost completely fenced, small shed for lawn/garden equipment. BRING ALL OFFERS!

Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-360-7777)

Listing Agent: Kathy Liga (941-920-6070)

Remarks: Under contract-accepting backup offers. Stunning and move-in ready, this beautifully renovated and fully furnished 2-bedroom, 2-bath condo offers effortless living in an exceptionally convenient central Sarasota location. Perfectly positioned in the heart of the city, you are just minutes from Downtown Sarasota, Sarasota Memorial Hospital, and a straight drive to Siesta Key’s world-famous beaches. Enjoy the rare combination of accessibility and everyday walkability, with popular dining, cafés, and entertainment only a short stroll away. Inside, the condo has been updated to the nines, showcasing a bright, naturally light interior and a complete 2023 renovation including a modern kitchen with quartz countertops and breakfast bar, fully renovated bathrooms, updated flooring throughout, impact (hurricane-rated) windows, and custom window treatments. Offered fully furnished and move-in ready, this residence is ideal for seasonal living, downsizing, or anyone seeking a low-maintenance Sarasota retreat. Ground-floor convenience, a quiet private setting, parking directly outside the unit, and the added benefit of not being located in a flood zone further enhance the appeal. The community pool and laundry facilities are just steps away, adding to the ease of everyday living. Located within a desirable 55+ community, this condo delivers comfort, simplicity, and exceptional lifestyle appeal. Spend your time enjoying Sarasota’s favorite attractions while living in the heart of the city — mornings on Siesta Key’s world-renowned beaches, afternoons exploring local markets and boutiques, and evenings spent dining at the area’s exceptional restaurants. The property can be rented after 1 year of ownership with 4 month lease minimums - no pets allowed. Schedule your tour today!

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

Listing Agent: Ryan Adamson, Pa (941-713-9234)

Remarks: Under contract-accepting backup offers. Gulf-front luxury townhome with private beach access on Siesta Key! Soak in the breathtaking, unobstructed views of the Gulf and iconic Siesta Beach from every level of this three-story, turnkey-furnished townhouse-style condominium. Just a short distance from the sand in the intimate, nine-residence enclave of Tiffany Sands, this rare Siesta Key offers blends relaxed beachside living with elegant design and modern comforts. Spanning 2,611 square feet, this three-bedroom, 3.5-bath residence welcomes you with an open-concept main floor that seamlessly connects the kitchen, dining and living areas—all framed by floor-to-ceiling impact-rated sliding glass doors and panoramic Gulf vistas. The living room is anchored by a cozy wood-burning fireplace and enhanced by crown molding, recessed lighting and sleek ceramic tile flooring. Go onto the expansive Gulf-front balcony, an ideal setting for alfresco dining or sunset lounging. The kitchen is stylish and functional, featuring solid-surface countertops, stainless steel appliances, modern cabinetry with pullout shelving, under-cabinet lighting and a breakfast bar for casual meals. Upstairs, the spacious Gulf-front primary suite offers postcard-worthy views, a private balcony, sitting area, double closets and a luxurious en-suite bath with jetted soaking tub, double vanity, separate shower, bidet and two skylights. Two additional guest bedrooms—flexibly configured with a retractable dividing wall—are also on the third floor along with a full guest bath and a well-equipped laundry room. The oversized ground-floor bonus room opens via sliding glass doors to a covered patio just steps from your private beach path. A full bath with walk-in shower was stylishly updated in 2024, making this level ideal for guests, a home gym or media lounge. Additional highlights include a one-car attached garage with extra storage, newer water heater (2024), HVAC (2022), roof and skylights (2017), hurricane shutters and flexibility of 30-day minimum rentals. Just .4 miles from Siesta Village’s vibrant shops and dining, and Siesta Beach Park, this exceptional home delivers the ultimate island lifestyle—whether you’re seeking a serene personal retreat, a seasonal escape or a savvy investment property.

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

Listing Agent: Mike Warm, Llc (941-525-2740)

Remarks: Under contract-accepting backup offers. Spacious and thoughtfully designed, this 4-bedroom, 4-bath home in South Gate offers a rare combination of size, layout, and value. Major components have already been addressed with copper wiring and PVC plumbing, providing added peace of mind. Vaulted ceilings, built-ins, and new skylights enhance the light-filled interior. The well-proportioned floor plan includes three en-suite bedrooms plus a private 600 sq. ft. upstairs suite with sitting area, kitchenette, and electric fireplace—ideal for guests, in-laws, or teens seeking separation and space. The primary suite offers a jetted soaking tub with shower, separate water closet, multiple closets, and a foyer area well suited for a desk or reading nook. The main living area flows seamlessly to the kitchen and dining spaces, while the fenced backyard offers room to play, garden, or create an ideal outdoor retreat with space to add a pool. Located within Sarasota’s highly rated school district and just minutes to Siesta Key Beach, downtown, and shopping, this home delivers comfort, functionality, and location in one compelling opportunity.

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

Listing Agent: Sherri Mills (941-350-7112)

Remarks: If you have been searching for a property in Sarasota that pairs an unbeatable golf course location with the peace of mind that comes from a fully updated home, this is it. Tucked away in the desirable Village Green Estates, this 3-bedroom, 4-bathroom residence is positioned on a premier lot that offers sweeping, private panoramic views of the greens. Unlike many homes in the area, the major heavy lifting has already been completed, including new hurricane impact windows (2025), a fresh HVAC system (2024), updated plumbing (2019), and a tile roof (2018). The layout is designed for the Florida lifestyle, featuring a rear screened patio. Inside, triple pocket sliding doors disappear to merge the interior living space with the scenic outdoor backdrop. A standout feature of this floor plan is the versatile "suite-within-a-suite"—a large bonus room attached to the primary bedroom with its own full bath and private exterior entrance. Whether you need a dedicated home office, a nursery, or a guest wing, this space adapts to your needs. The location offers a rare combination of convenience and low-cost living with NO CDD fees and a remarkably low $100 annual HOA fee. You are just minutes away from the Legacy Bike Trail, UTC Mall, Downtown Sarasota, and the white sands of Siesta Key, with daily essentials like Publix and Starbucks right around the corner. This is a rare opportunity to secure a high-quality, move-in-ready home on the golf course without the high carrying costs of a typical country club.

Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)

Listing Agent: Ana Mitchell (813-599-4669)

Remarks: Under Construction. Welcome home to The Wagoner, by David Weekley homes, in the brand-new, suburban lifestyle community of Lakeview Crossing in Sarasota. This single-story home sits peacefully on a pond where you can imagine coming home to serene views with sightlines of the pond from the moment you walk in the front door. Once inside, you’ll notice the thoughtfully designed open concept, flooded with natural light and a designer kitchen that will make hosting gatherings a must. The coastal interior design selections make you feel like you're just steps away from the beach. The owner’s retreat is situated off the back of the home, split from the other bedrooms, so you will have your own private oasis to wind down in. In addition to the 4 bedrooms, there is a dedicated den with French doors giving you flexible options with how to use the extra space. The 3-car tandem garage gives you plenty of storage and space to park all your vehicles, and the dedicated indoor utility room allows you to never break a sweat when doing laundry. Enjoy your morning coffee or evening glass of wine out back on your extended lanai or even on the spacious front porch where you can watch the kids play. Also, you are conveniently located close to downtown Sarasota (10 miles), UTC shopping center (9.4 miles), Siesta Key Beach (12 miles) & SQR airport (15 miles). Enjoy peace of mind knowing your home is constructed by the award winning builder of David Weekley Homes with energy efficiency in mind.

Listing is courtesy of: WEEKLEY HOMES REALTY COMPANY (866-493-3553)

Listing Agent: Robert St. Pierre

Remarks: One or more photo(s) has been virtually staged. Siesta Key Waterfront Retreat – Walk to the Beach & Village! Ready for immediate enjoyment this winter, this 3-bedroom, 2-bath Key West–inspired home embodies the essence of the Siesta Key lifestyle—boating from your backyard and strolling to the powdery white sands and vibrant Siesta Key Village with its renowned dining, boutiques, and nightlife. Nestled on a quiet cul-de-sac, this canal-front retreat offers 100 feet of waterfront, a covered 5,000-lb boat lift, and direct access to the Intracoastal Waterway. The expansive outdoor living area invites relaxation and entertaining with a heated pool featuring a cascading stone waterfall, covered bar & and wide open fenced area surrounded by tropical landscape creating a private island ambiance. Inside, a neutral palate, high ceilings, and open layout feels light and airy. The white kitchen features granite countertops, stainless steel appliances, dual sinks, a center cooking island, and a breakfast bar perfect for casual dining. Warmth and character is further enhanced by a marble fireplace in the main living and dining areas. The primary suite offers a peaceful retreat with an ensuite bath, dual vanities, a walk-in shower, and a charming window seat. Guests & children have their own wing with a full bath and a convenient laundry room. Enjoy peace of mind with impact windows, hurricane-rated doors, and major upgrades including a metal roof, Trex decking, Nichiha siding, and reinforced lanai. Positioned at one of the highest elevations on the street, the home has never experienced flooding. And there’s an additional ground floor BONUS…a generously sized sunlit air-conditioned play & storage room! Whether you’re searching for a seasonal escape, a full-time residence, or a property with strong vacation rental appeal, this move-in-ready home offers exceptional versatility and potential.

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

Listing Agent: Ryan Ackerman, Pa (305-205-7700)

Remarks: Under contract-accepting backup offers. Motivated seller and a huge price adjustment! Rarely available in Nottingham! Tucked away on a quiet cul-de-sac with 140 feet of sparkling lake frontage, this 3-bedroom home is perfectly designed for enjoying Florida’s outdoor lifestyle. The living room, kitchen/family room, and primary suite all open to the expansive screened lanai, featuring a 22’ x 42’ open area plus a 12’ x 32’ covered space—ideal for entertaining or simply relaxing by the pool. The first-floor primary suite offers a 10’ x 5’ walk-in closet and an en suite bath, while two additional bedrooms are located upstairs for added privacy. The kitchen flows into the family room with its cozy corner fireplace and soaring vaulted ceiling leading to a second-floor loft. Recent updates include fresh interior paint, reinforced and leveled pool decking with a 5-year warranty, and a new pool pump and filter. While some finishing touches remain—such as resurfacing the pool deck and replacing the skimmer—this home presents a fantastic opportunity to create your own retreat in one of the area’s most desirable neighborhoods. Don’t miss the chance to make this Nottingham gem your own!

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

Listing Agent: Larry Brzostek (941-993-3125)

Remarks: Under contract-accepting backup offers. One step away from Siesta Key, Sarasota Memorial and Hillview. West of the trail. Beautiful condo in Oasis on Osprey. Enjoy the community pool before you head to the beach.2 bedrooms, 2 bathrooms. large living area. Screened lanai. All tiled for easy maintenance. Granite countertop in kitchen. AC 2020.

Listing is courtesy of: INVESTUS REALTY LLC (941-538-2010)

Listing Agent: Vincent Ricaud (941-538-2010)

Remarks: Discover the pinnacle of direct bayfront excellence blending sculptural modern form with water views. Full-floor residence at AQUA is one of only eight in Sarasota’s most exclusive boutique building found on Golden Gate Point. Perched on the sixth floor with 180° views of Sarasota Bay and the iconic Ringling Bridge, this home offers a level of elegance and customization rarely found—even in new construction. From the moment you step off your private elevator into the foyer, the residence unfolds with simple, clean lines spotlighting floor-to-ceiling 10-foot glass walls which frame the Bay & Sunsets like living artwork. More than $500,000 in curated upgrades elevate the interiors, transforming this barely lived in 4,100+ sq ft space into a truly one-of-a-kind lifestyle rarely found in Sarasota’s market. Open-concept layout lives like a single-family home with distinct entertaining areas, a stunning waterfront dining room, and a bespoke wet bar. Chef’s kitchen is a study in form and function, seamlessly integrated into the living space while offering top-tier appliances and finishes: Wolf cooktop and ovens, 2 Miele dishwashers , Sub-Zero refrigerator, Cuisines Laurier cabinetry with a 9 ft expansive island topped with striking Cielo quartzite. Private primary suite is designed as a serene escape, featuring stunning water views, custom walk-in closets uniquely designed with two separate individual sections of sleek Cuisimax poly-gloss doors and packing station. Elevated features in the spa-style bathroom include dual vanities topped with striking azure crystal marble, a soaking tub, and a large glass-enclosed shower Two generous guest suites offer en-suite privacy, while a fourth bedroom currently serves as a sleek office. With discreet concierge services found only in a 5-star boutique style building, Aqua offers an enclosed oversized private two-car garage with an EV charging station & dehumidifier, private boat dock that accommodates 36' boat + flat kayak lift, temperature-controlled wine storage/wine tasting room, fitness studio, heated pool and spa and meeting room. Be part of vibrant downtown living in a secluded quiet location.

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

Listing Agent: Ryan Ackerman, Pa (305-205-7700)

Remarks: Introducing “Gatsby Manor,” set along Hillview Drive, one of Sarasota’s most coveted bayfront addresses, often compared to Port Royal for its exclusivity and waterfront lifestyle, this rare Harbor Acres estate property spans nearly three-quarters of an acre on deep, boatable water with sweeping, unobstructed Sarasota Bay views stretching south toward Siesta Key and the Gulf of Mexico, representing one of the neighborhood’s most distinguished open-bay offerings where only a select few residences achieve true estate scale. Encompassing more than 8,000 square feet of air-conditioned space with four bedrooms and three-and-a-half baths. The residence is complemented by a grand motor court accommodating 15+ vehicles beneath a canopy of majestic grand oaks. Privately approached through wrought-iron gates and a sweeping circular drive anchored by a multi-tiered fountain, the home opens to a dramatic two-story foyer framing the water beyond. Interiors are defined by soaring ceilings up to 22 ft. in height, exceptional millwork, multiple fireplaces, a striking two-story wood-paneled library, formal dining with 12-foot ceilings, and a wetbar—perfectly blending elegant entertaining with comfortable daily living. The chef’s kitchen is designed to support both everyday living and large-scale gatherings, featuring double 36-inch Sub-Zero refrigerators with dual freezer drawers, two dishwashers, and a 60-inch Wolf gas range with six burners and infrared dual griddle. The owner’s suite occupies the entire east wing of the main living level, creating a private waterfront retreat complete with a gas fireplace, sitting area overlooking the pool and bay, dual walk-in closets, and a spa-inspired bath highlighted by a sculptural copper soaking tub, dual vanities, and a dedicated luxury makeup area. Upstairs, a second primary-style suite and two additional guest bedrooms are accessed via the grand staircase or three-stop elevator, offering privacy and flexibility for family and guests. The 3,800+ square-foot ground-level bonus area serves as the home’s ultimate entertaining environment, featuring a remarkable speakeasy lounge and an impressive 700+ bottle wine room. This expansive space functions as a true extension of the residence’s living experience—ideal for hosting gatherings, intimate evenings, or celebrations on a grand scale. Outdoor living is equally exceptional, centered around an expansive marble terrace surrounding the 25’ × 60’ heated saltwater pool with integrated sun shelf and spa. A brand new deep-water dock with a 20,000 lb. boat lift and seawall replaced in 2017 further enhance the property’s boating capabilities and long-term value. Additional highlights include hurricane-rated garage doors, elevator access to all three levels, a drive-through three-car garage, and extensive storage throughout. Perfectly positioned just a short stroll to Southside Village’s restaurants and boutiques, minutes from downtown Sarasota’s celebrated arts and cultural district, and only four blocks from Sarasota Memorial Hospital. Gatsby Manor offers a truly rare opportunity to enjoy estate-scale open-bay living with deep water, privacy, and exceptional walkability in one of Sarasota’s most prestigious waterfront neighborhoods.

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

Listing Agent: Ryan Ackerman, Pa (305-205-7700)

Remarks: Spacious and beautifully updated 5-bedroom, 2-bath pool home in the heart of Sarasota—offering no deed restrictions, no HOA, and no flood insurance required. This fully rehabbed home welcomes you with a bright living room featuring stunning designer metallic flooring. The flexible 5th bedroom is currently used as a home office, perfect for today’s lifestyle. Major updates include a metal roof (2012) and new HVAC system (2025) for peace of mind. The kitchen shines with new appliances, designer-added storage units, and a striking palm frond tile backsplash, creating both style and functionality. The dining room features a built-in closet with a charming barn door closure. Enjoy added convenience with an indoor laundry room equipped with a tankless water heater. The home is fully fenced for privacy and includes ample outdoor storage, along with new shutters throughout for enhanced curb appeal. Step outside to your private pool area—ideal for relaxing or entertaining. This home is being sold partially furnished, making it move-in ready or a great investment opportunity. Centrally located near the interstate, hospitals, medical facilities, shopping, and a wide variety of dining options. A rare opportunity to own a 5-bedroom pool home in Sarasota priced below market—don’t miss it!

Listing is courtesy of: BRIGHT REALTY (941-552-6036)

Listing Agent: Geri Scheckner (941-356-0652)

Remarks: An exquisite, fully updated, fully furnished 2 bedroom 2 bathroom beach oasis! Located in the heart of Siesta Key at the exclusive upscale Gulf & Bay Club. Featuring high end detailed finishes and interiors professionally crafted to perfection. This unit is in C Building with direct beach access just steps away from your front door. Enjoy breath taking sunsets from your personal balcony or head down to the private beach for an up close view of the #1 beach in the US. The sandy white powder stretches 800 feet across this pristine 32 acre meticulously cared for tropical community. You will be impressed with world class amenities offered at Gulf & Bay Club. Enjoy the comfort of 24 hour gated security, heated pools, a fitness center, dry saunas, hot tub, tennis courts, just to name a few. Multiple barbecues and tiki hut picnic areas are great for entertaining your guests. The amenities don’t stop there, the club house has a library, bar, pool table and TV's all for your enjoyment. Not to mention the electric car charging stations and on site car wash. You are moments away from Siesta Village to enjoy alfresco dining with live music, specialty shopping and more! Take a short trip to the mainland and discover theater, art and fine dining. This is the island resort lifestyle you have been looking for, don't let your chance of fine beach living slip away.

Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)

Listing Agent: Sylvia Wilk (630-863-1825)

Remarks: Experience the best of beachfront living at Lido Ambassador with this rarely available 6th-floor residence, lovingly maintained by long-time owners and offering captivating Gulf views, impact-rated windows and sliders, and endless potential to personalize. Perfectly situated on the sandy shores of Lido Beach and just moments from world-famous St. Armands Circle, this condo offers the ideal balance of coastal tranquility and vibrant Sarasota living. This two-bedroom, two-bath unit features a desirable split floor plan, open living/dining area, and a private balcony where you can soak in breathtaking sunset views, sea breezes, and the ever-changing colors of the coastline. Meticulously cared for over the years, this home is move-in ready or the perfect canvas to update to your personal style. The spacious primary suite offers ample closet space and an en-suite bath, while the guest bedroom and bath provide a private retreat for visitors. Natural light, a thoughtful layout, and the overall condition reflect the pride of ownership throughout. Lido Ambassador is a well-managed community of just 74 residences, known for its pristine grounds and attentive upkeep. The Gulf-front heated pool and sun deck are currently undergoing a full renovation, soon to reopen better than ever, with a refreshed, resort-style atmosphere for residents to enjoy. Additional amenities include a fitness center, catering kitchen, private storage, and assigned covered parking. Steps from the Lido Beach Resort Tiki Bar and short distance of St. Armands Circle, Longboat Key, and the arts and culture of downtown Sarasota, this location is unmatched. Whether you’re seeking a coastal getaway, investment opportunity, or full-time residence, this 6th-floor unit delivers exceptional location, views, and value. Discover why Lido Ambassador is one of the most coveted addresses on Lido Key.

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

Listing Agent: Lindsay Nock (941-735-7005)

Remarks: Residence 1013 at The Mark Sarasota offers a rare combination of comfort, convenience, and newer construction in the heart of downtown. Built in 2019, this residence provides modern peace of mind with impact hurricane glass and exterior doors, along with soaring 10-foot ceilings and a bright, open feel throughout. The home includes two deeded side-by-side covered parking spaces located just 20 feet from the elevator, an exceptional convenience rarely found downtown. Positioned on the quiet and highly desirable side of the building, the residence enjoys southern exposure and beautiful views overlooking the pool, with sightlines extending toward Sarasota Bay and the Gulf of Mexico. Set on the 10th floor, this thoughtfully designed layout features two bedrooms plus a den and two-and-a-half baths across 1,577 square feet, along with a covered terrace that extends the living space outdoors. The split-bedroom floor plan provides privacy while maintaining an open, functional flow ideal for both everyday living and entertaining. Walls of glass fill the home with natural light and frame tranquil views over the treetops toward Paul Thorpe Park and the Mermaid Fountain. The kitchen blends style and function with imported cabinetry, stone countertops, designer backsplash, stainless steel appliances, and an upgraded induction cooktop. It connects seamlessly to the main living and dining areas, creating an inviting space to gather. A full-size utility room with additional storage adds everyday practicality. The primary suite opens directly to the terrace and features a spacious walk-in closet and a well-appointed bath with illuminated mirrors and refined finishes. The guest bedroom is privately situated, while the den offers flexibility as a home office or additional lounge space. A climate-controlled storage unit located just down the hall provides added convenience. Residents enjoy The Mark’s resort-style amenities, including a heated saltwater pool and spa, outdoor seating and grilling areas, club room with catering kitchen, billiards, fitness center, yoga studio, and spin room. The building also offers a pet-friendly environment, 24/7 front desk staffing, secure lobby access, and overnight roving security. Located in the center of downtown Sarasota, the residence places you just steps from the renowned Sarasota Farmers Market and only two blocks from Whole Foods Market. Cultural attractions including the Sarasota Opera House, Florida Studio Theatre, and Selby Public Library are all within easy reach, along with dining, galleries, and the waterfront. Surrounded by exciting new luxury developments, including the nearby Waldorf Astoria Residences Sarasota, this location continues to elevate as one of downtown’s most sought-after areas. Don’t miss the opportunity to own a newer-built residence in one of Sarasota’s most vibrant and walkable neighborhoods.

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

Listing Agent: Ryan Ackerman, Pa (305-205-7700)