Homes for Sale Near Brookside Middle in Sarasota - 743 homes

Remarks: Welcome to 3049 Gypsy Street, a beautifully updated, coastal-inspired retreat being offered turnkey furnished (minus personal property), making it the perfect opportunity for a first-time homebuyer, snowbird or savvy investor looking for immediate income potential. Previously operated as a highly rated Airbnb, this charming Sarasota home is move-in ready and set up to continue generating rental income from day one. Inside, discover a light and bright interior featuring luxury vinyl plank flooring throughout, a spacious living and dining area and a stunning remodeled kitchen complete with white cabinetry, stainless steel appliances, a farmhouse sink, a beautiful white 3D backsplash and all appliances included. The split-bedroom layout offers two spacious bedrooms and two completely renovated baths. The primary suite features a brand-new bath with a large walk-in shower, while the guest bedroom comfortably accommodates multiple guests with a full and twin bed. Outdoor living shines with a charming covered coastal-style lanai complete with a ceiling fan, shell paver patio area, fully fenced backyard, new landscaping and plenty of room for a future pool. There is also separate RV/boat parking on the side of the home for added flexibility or plenty of room for a pool. Additional highlights include a new roof (2022), a sewer connection completed in 2021, a one-car garage with a washer, dryer, utility sink and storage. Turnkey furnished opportunity: this was previously a successful Airbnb with a rental history. Ideally near all Sarasota has to offer, including world-famous beaches, dining, shopping, arts and entertainment, this adorable coastal getaway offers a blend of lifestyle and investment opportunity.

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-907-9541)

Listing Agent: Jaci Krawtschenko (941-284-3789)

Remarks: Under contract-accepting backup offers. Charming Coastal Oasis in the Heart of Siesta Key Nestled on a serene, tree-lined property, this inviting 4-bedroom, 3.5-bath beach-style home offers the perfect blend of tranquility, charm, and central location. Step into a spacious, light-filled living area with an open kitchen layout—ideal for hosting friends and making family memories. Freshly updated with new paint, gleaming quartz countertops, and stainless steel appliances, this move-in-ready home is designed for easy, coastal living. The open floor plan includes a spacious upstairs primary suite with French doors leading to a private balcony—your own quiet retreat. Three additional guest bedrooms are thoughtfully located on the first floor, including a separate guest suite with its own private entrance, offering comfort and flexibility. Step outside into your private backyard oasis featuring a beautiful pool and spa, fully enclosed with a lovely paver deck—perfect for relaxing, entertaining, or enjoying sunny Florida days in peace and privacy. There's still plenty of yard space to garden or play. Slip on your sandals for a short stroll to the world-famous Siesta Key Beach, ranked #1 in the U.S. by TripAdvisor, or bike to the charming Siesta Key Village with its eclectic mix of shops, restaurants, and entertainment. Don’t miss this peaceful, spacious retreat—your own slice of paradise on Siesta Key.

Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)

Listing Agent: Dianne Anderson (941-350-3513)

Remarks: Under contract-accepting backup offers. Beaches, Boating & Bistros!!! Excellent Investment, 2nd Home or Build new. Island Style Canal Front Home on Siesta Key, steps to World Famous Siesta Village & the cool quartz sands of Siesta Beach. This Island Style 2 bed, 2 bath home in close proximity to all the food & exciting nightlife that Siesta Key has to offer. 1 car garage. This home on a Cul de sac is light & bright with Terrazzo floors for the laid-back Island lifestyle. New roof in 2022. Excellent rental potential with its ideal location makes this property a solid investment. Out back is a huge deck on the Canal that is perfect for waterfront get togethers. Updated kitchen with stainless steel appliances that opens up for entertaining with family & friends. Separate laundry room and a potting shed & workshop. After spending the day on your boat, either cook up your catch or stroll to your favorite Siesta Village establishment. Or, better yet, take a stroll on the Beach & enjoy Sunset.

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

Listing Agent: Dan Miller (941-376-7442)

Remarks: ***Potential for $150k+ gross income. Zoned for weekly rentals. ONE UNIT IN CONDO COMMUNITY*** Escape to the ultimate Siesta Key lifestyle with this rarely available, coastal contemporary condo—offering the perfect blend of luxury, privacy, and convenience with direct access to the sugar-white sands of world-renowned Siesta Key Beach and Crescent Beach. Known for its quartz-crystal sand and turquoise waters, this top-rated beach offers stunning sunsets, gentle waves, and vibrant coastal charm, all just a short stroll from your door. Nestled in a boutique enclave of only five residences, this exclusive unit has fresh interior paint, lives like a single-family home and is one of only two in its building. This unit encompasses the entire floor and shares no walls with other units. With five private patios, a built-in outdoor grill, tall ceilings and windows, and plantation shutters throughout, the light-filled layout offers an open flow between living, dining, and kitchen spaces—accented by custom cabinetry, upscale finishes throughout. The spacious primary suite provides a private retreat, while the entire home is thoughtfully designed on one level for effortless living. A private elevator offers direct access from your oversized ground-level garage, which is nearly 1,000 square feet and accommodates three vehicles plus storage, along with a private driveway for guest parking — a rare find on the Key. This property is zoned for short-term, weekly rentals and boasts a strong rental history, making it an exceptional opportunity for both personal enjoyment and possibility to earn over $150,000 in investment income. Enjoy walkable access to beachside boutiques, island restaurants, and boat rentals, plus quick and easy access on and off the island, making it ideal for both full-time living and a low-maintenance vacation home. Shared amenities include a serene pool, private owner's clubhouse, and common area used by only five residences, ensuring a peaceful and private setting. Whether you're searching for a serene retreat or a stylish beach escape with income potential, this home offers a unique opportunity to live in the heart of Siesta Key’s coastal paradise. Furnishings optional - not included in list price.

Listing is courtesy of: HARTMAN REAL ESTATE & COMPANY (941-500-4547)

Listing Agent: Zain Hartman (941-735-6415)

Remarks: Under contract-accepting backup offers. Multiple Offers. Seller requests highest and best offers by 8pm on May 10. Nestled behind the gates of The Landings, one of the only gated communities "West of the Trail", this custom Florida-style home offers the perfect blend of timeless elegance, spacious living, and an exceptional Sarasota lifestyle. Situated on a desirable corner lot with easy access to the members-only gate, this beautifully updated home spans more than 3,100 square feet and features four bedrooms, three-and-a-half baths, a three-car garage, bonus room, and an upstairs loft area ideal for flexible living. Designed with an open, airy feel and soaring high ceilings, the home is filled with natural light and inviting living spaces perfect for both everyday comfort and entertaining. The expansive screened lanai showcases two separate sitting areas, an outdoor kitchen, a large heated pool with recent resurfacing, and views of the spacious backyard, the benefits of being a corner lot, creating a true private retreat. Inside, the thoughtfully designed floor plan features a rare first-floor primary suite, a highly sought-after feature for a two-story home in The Landings. The updated kitchen is the heart of the home, complete with a large center island perfect for gathering with family and friends while creating lasting memories. Updated bathrooms, a cozy fireplace in the living room, fresh interior and exterior paint, further enhance the move-in-ready appeal of this exceptional property. Residents of The Landings enjoy tree-canopied streets, a private nature trail leading to Roberts Bay, and optional membership to the Landings Racquet Club, featuring tennis, pickle ball, a heated pool, fitness center, and clubhouse. This prestigious gated community of 702 residences borders the Intracoastal Waterway and spans 280 acres with stand-alone homes, villas, and town-homes surrounded by 75 acres of protected mangroves, nature preserves, walking trails, a gazebo, kayak launch, and butterfly garden. Take your golf cart to the Landings Shopping Center which features, Publix grocery store, Starbucks, and numerous dining options from breakfast hot spots to outstanding seafood options. Ideally located near A-rated schools, Southside Village, Sarasota Memorial Hospital, and Sarasota’s renowned dining, arts, and waterfront attractions, this is a rare opportunity to own a beautifully updated home in one of Sarasota’s most desirable gated communities. Located in flood zone X, the highest zone, no flood insurance required.

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

Listing Agent: Thomas Hedge, Jr (941-587-6660)

Remarks: $$ 10,000.00 in closing cost's paid for by the SELLER. Like new and upgraded gorgeous condo. Minutes from world famous Siesta Key Beach and safely located in flood zone X. All new vinyl plank flooring in living areas and new carpet in bedrooms. Both bathrooms are newly renovated, freshly painted inside and out, along with a total makeover of the kitchen in 2025. Located in the rear of the development this condo is very quiet and secure. New washer and dryer, make this as good as a new unit. Ceiling fans and skylights keep it light and bright inside. Community heated pool and fitness center are open to the residents at their leisure. Clubhouse includes kitchen, fitness center, pool table and rest rooms with showers. Lanai features fully enclosed glass windows with screens, new storm doors front and rear. Gardener's paradise in the rear with lush tropical plants. In front enjoy your reserved private parking spot. Close to shopping and some of the best restaurants in Sarasota.

Listing is courtesy of: DENNIS REALTY & INV. CORP. (813-949-7444)

Listing Agent: John Pinta (813-390-4918)

Remarks: Welcome to a home that lives like a resort in Sarasota’s premier neighborhood, Harbor Acres. With 134 feet of water, this nearly 12,000-square-foot estate is crafted for laid-back luxury and everyday ease, designed for entertaining against breathtaking views of Sarasota Bay, the Ringling Causeway, and the downtown skyline. A paver driveway winds through mature palms to a stone exterior with travertine steps, a porte cochere, and an expansive porch, all setting the tone for within. Solid wood doors open to a soaring foyer with wood columns, intricate millwork, and custom archways that reflect the home’s detailed character. Designed for easy living, the main spaces flow effortlessly, highlighted by a family room with zero-corner sliders, a wall of windows overlooking the water, a coffered wood ceiling, and a stone fireplace that anchors the room. Detailed trim, crown molding, and wood wainscoting add depth and highlight craftsmanship throughout. The kitchen is anchored by a large island with storage, prep space, and a sink, and equipped with top-tier appliances including Dacor double ovens and range, Sub-Zero refrigerator and freezer, dual Bosch dishwashers, a warming drawer, and a Scottsman ice maker. A walk-in pantry with custom shelving keeps everything organized, while the adjacent butler’s or catering kitchen, with its own cooktop, refrigerator, microwave, and desk area, makes entertaining effortless. An eat-in area with an aquarium window and bar-height counter seating keeps it functional and inviting. A wine room with wood-paneled walls and a separate entertaining bar with an oversized wine cooler make this home ideal for gatherings of any scale. The theatre offers the ultimate at-home viewing experience with custom wall and ceiling treatments, tiered seating, blackout glass windows and door, and a built-in bar with sink and additional seating. Outside is an extension of the home’s lifestyle, offering resort-style features meant for everyday use. The pool features a sun shelf, stone accents, and cascading water features paired with a raised spa, while the outdoor kitchen, with grill, refrigerator, and bar seating, makes entertaining effortless. A dedicated pool bath adds convenience, and nearby, the turf yard, fire pit, and hammock invite easy relaxation. A spiral staircase connects the primary suite terrace to the outdoor amenities, and a private dock completes the experience. Back inside, the home offers a thoughtful blend of privacy and flexibility. The primary suite is a retreat with incredible views, French doors to a private terrace, a coffee bar, and a sitting room with a fireplace. Its spa-inspired bath features a jetted tub, multi-head shower, custom dual vanity, and dual walk-in closets. A separate in-law suite provides full independence with its kitchenette, living room, laundry, and terrace. Guests enjoy four additional suites with private baths, a bonus room with a terrace, a fitness room, a built-in homework area, and easy access across all levels via dual staircases and a three-stop elevator. Abundant garage and storage space complete the estate. This Harbor Acres residence delivers the ultimate Sarasota lifestyle, just minutes from downtown, Southside Village, and Gulf beaches. The adjacent vacant lot at 1435 Hillview is currently offered separately, with the opportunity to purchase both together. Bank signoff on the sale of this property may be required. The gate and driveway would need to be reconfigured.

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

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

Remarks: Welcome to a home that lives like a resort, set on two lots consisting of 1.8 lush, waterfront acres in Sarasota’s premier neighborhood, Harbor Acres. Crafted for laid-back luxury and everyday ease, this nearly 12,000-square-foot estate offers 249 waterfront feet and is designed for entertaining, all set against views of Sarasota Bay, Ringling Causeway and the downtown skyline. An expansive paver driveway winds through mature palms to a stone exterior with travertine steps, a porte cochere and an expansive porch, all setting the tone for within. Solid wood doors open to a soaring foyer with wood columns, intricate millwork and custom archways that reflect the home’s detailed character. Designed for easy living, the main spaces flow effortlessly, highlighted by a family room with zero-corner sliders, a wall of windows overlooking the water, a coffered wood ceiling, and a stone fireplace that anchors the room. Detailed trim, crown molding, and wood wainscoting add depth and highlight craftsmanship throughout. The kitchen is anchored by a large island with storage, prep space and a sink, and equipped with top-tier appliances including Dacor double ovens and range, Sub-Zero refrigerator and freezer, dual Bosch dishwashers, a warming drawer and a Scottsman ice maker. A walk-in pantry with custom shelving keeps everything organized, while the adjacent butler’s or catering kitchen—with its own cooktop, refrigerator, microwave and desk area—makes entertaining easy. An eat-in area with an aquarium window and bar-height counter seating keeps it functional and inviting. A wine room with wood-paneled walls and a separate entertaining bar with an oversized wine cooler make this home ideal for gatherings of any scale. The theatre offers the ultimate at-home viewing experience with custom wall and ceiling treatments, tiered seating, blackout glass windows and door, and a built-in bar with sink and more seating, ideal for movie nights, game days or entertaining. Outside is an extension of the home’s lifestyle, offering resort-style features meant for everyday use. The pool features a sun shelf, stone accents, and cascading water features paired with a raised spa, while the outdoor kitchen, with grill, refrigerator and bar seating, makes entertaining effortless. A dedicated pool bath adds convenience, and nearby, the turf yard, fire pit and hammock invite easy relaxation. A spiral staircase connects the primary suite terrace to it all, while a versatile sport court and two private docks for 75-plus-foot yachts complete the experience. Back inside, the home offers a thoughtful blend of privacy and flexibility. The primary suite is a retreat with incredible views, French doors to a private terrace, a coffee bar and a sitting room with a fireplace. Its spa-inspired bath features a jetted tub, multi-head shower, custom dual vanity and dual walk-in closets. A separate in-law suite provides full independence with its kitchenette, living room, laundry and terrace. Guests enjoy four more suites with private baths, a bonus room with a terrace, a fitness room, a built-in homework area, and easy access across all levels via dual staircases and a three-stop elevator. Abundant garage and storage space complete the estate. This Harbor Acres home delivers the ultimate Sarasota lifestyle, just minutes from downtown, Southside Village and Gulf beaches. The vacant lot at 1435 Hillview can be separated and the list price reduced accordingly.

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

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

Remarks: ***5% financing for qualified buyers for two years. Seller will buy down your mtg. rate for two years to only 5% - FURNISHED*** Discover your perfect slice of paradise in sunny Sarasota! Whether you're looking for a relaxing getaway, a full-time residence, or a smart investment opportunity, this charming condo checks all the boxes. Situated in a welcoming, pet-friendly community, this home offers a thoughtfully designed layout, ideal for individuals or couples. The condo comes fully furnished, including a 63” HD TV in the living room, a 43” HD TV in the bedroom, a fully equipped kitchen, and all linens. With new wood floors and updated kitchen and bath fixtures, everything you need is ready for you to settle right in or start renting immediately. Enjoy low HOA fees, a heated swimming pool, and a clubhouse, all within close walking distance and set in a well-maintained community. The sellers have fully covered the special assessments, adding even more value. Conveniently located with biking distance to Sarasota’s top destinations—including the breathtaking Siesta Key Beach, cultural hot spots, shopping, and dining—this property provides easy access to everything you need. Seize this chance to own a beautiful condo and embrace the best of Florida living! This second-floor walk-up means no flooding issues. Sienna Park roofs were replaced in 2023, and all special assessments have been paid in full by the seller. At 768 sq ft, this is the largest of the one-bedroom units in the complex—compare it to the smaller 555 sq ft one-bedroom units. Walking distance to Publix and public transportation. Furnished except for a few personal items.

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

Listing Agent: Ron Koelling (941-923-4616)

Remarks: Under contract-accepting backup offers. This charming 2-bedroom, 2-bath plus bonus room villa is nestled in the quiet and desirable Woodside South community in the Gulf Gate area of Sarasota. Ideally located just minutes from world-renowned Siesta Key Beach, with easy access to Interstate 75, and surrounded by a variety of restaurants, shopping, and premier golf courses, this home offers both convenience and a relaxed Florida lifestyle. The low maintenance fee includes water, trash, basic cable, pest control, exterior maintenance, and landscaping—making for truly easy living. This villa boasts larger square footage than many others in the community and features a spacious, light-filled living room, a kitchen with a cozy eating area, a primary suite with a full bath and walk-in closet, a second bedroom, and an additional full bathroom. A versatile den/office with a private exterior entrance adds extra flexibility for work or guests. Enjoy tile flooring throughout for a clean, modern feel. Residents also have access to a community pool and clubhouse—perfect for relaxing and socializing. Tenant's lease ends 4/30/2026.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Kate Aumua (305-542-5452)

Remarks: It's all about THE VIEW and the Direct Beach Access!!!  This first floor condominium has a Full Gulf View from the living room and glassed-in lanai. The water views are amazing, and the sunsets are gorgeous! You will walk out your front door right down to the sand to enjoy the warm Gulf water in minutes. There was no water intrusion and no water damage to this unit in past storms, as there are enough steps up from the level of the beach sand to make it elevated! Or use the ramp for easy luggage access.  The windows and doors are all wind and impact-rated, so you'll have peace of mind and a quieter home. All the floors are tile for easy care. The kitchen and bathrooms have been updated, including solid surface/granite counters and the elegant tiled showers.  Furnishings and appliances have been updated in the past year. This unit is move-in ready, or you can continue to rent it with a 3-night minimum for instant income (over $58,000 income after paying rental mgmt expenses in the first 9 months of 2025). On-site management is available for all your needs. The landscaping has been refreshed, there are new tables and chairs for outdoor dining or games, and beach chairs and chase lounges are provided, as well as shade under the condo's cabanas on the beach. Shuffleboard and corn-hole games await in the center greenway. The community pool is heated for your year-round enjoyment.  On the occasional rainy day, you'll enjoy the games in the club room (billiards, foosball, board games and puzzles). If you want to explore the Siesta Key Village shops, restaurants or nightlife, or explore Turtle Beach, just hop on the free trolley or other free ride-share vans. A 20-minute drive will take you to downtown Sarasota, including shops, restaurants, access to off-shore fishing or tour boats, opera, symphony, art museum, ballet, and live theater. With easy access to I-75, airport, colleges, Lifelong Learning, wine and spirits-tastings, and multiple parks and the Legacy Trail for biking, jogging, or skating, Sarasota and Siesta Key have it all!  This condo is your key to the fun, so bring your toothbrush and swim suit and ENJOY IT ALL!

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

Listing Agent: Susan Keal (941-320-1689)

Remarks: WELCOME to this beautifully UPGRADED 1 bedroom, 1 bath condo in Lucaya Country Club Villas!!! From the moment you arrive, you'll appreciate the attention to detail, starting with the painted and SCREENED front porch, perfect for year-round enjoyment. Step inside to an inviting open floor plan featuring spacious living room and dining room combo. The kitchen has been tastefully upgraded with MODERN cabinets, countertops, and an eat-in area with stools. The spacious bedroom offers ample closet space, while the bathroom includes a tub and shower combo for convenience. Throughout the condo, you'll find LUXURY VINYL FLOORING, adding to both style and durability. As part of Lucaya Country Club Villas, you'll enjoy access to a community pool, along with a prime location just a short drive to amazing restaurants, shopping, Sarasota's downtown vibrant scene, Sarasota Airport, Siesta Key and the WORLD FAMOUS GULF beaches. Whether you're searching for an investment property or a primary residence, this condo is exactly what you're looking for. This home is truly MOVE-IN ready, offering comfort, charm, and a maintenance-free lifestyle in a desirable community and it's waiting for you to enjoy! Don't wait to make this YOUR home and begin your FLORIDA Lifestyle!

Listing is courtesy of: SERHANT (646-480-7665)

Listing Agent: Christy Peterson (774-287-5322)

Remarks: Under contract-accepting backup offers. PRICED TO SELL AT $1,199,000 , this is your chance to own a home with incredible value. A NEW METAL ROOF IS SCHEDULED FOR APRIL -giving buyers instant peace of mind and long-term savings from day one. A rare offering with architectural character and privacy, this property presents exceptional value for buyers seeking a truly special one-of-a-kind retreat. Welcome to Storybook — a treetop sanctuary where architecture, nature, and artistry meet! Tucked away in Arlington park at the end of a private canopied road and surrounded by native Florida landscaping and protected wetlands, this extraordinary 3-bedroom, 4-bathroom residence with a custom library/den feels like a hidden world all its own. Designed by renowned Sarasota architect Richard G. Allen, known for his sustainable and expressive style, Storybook lives up to its name — enchanting, serene, and timeless. Soaring ceilings, exposed wood beams, and maple floors create a warm, open-concept living space that flows effortlessly to the outdoors. Clerestory windows invite natural light, while the wraparound porch and treetop pool immerse you in the surrounding canopy. A spiral staircase ascends to a light filled loft offering both inspiration and a tranquil retreat above it all. This home's heart resides in a custom library/den, a quiet sanctuary where books, ideas, and conversation gather. Beyond the cozy den lies an en suite bedroom, a serene space inspired by Zen simplicity. Sliding glass doors open to the wraparound patio, a haven for morning coffee and quiet reflection. On the same floor, a second primary suite welcomes you through an intricately hand carved door. Inside, an expansive bedroom and private sitting area rests quietly among the treetops, wrapped in peaceful seclusion. The ground floor includes a private guest suite and entrance, spacious laundry room, ample storage, oversized two-car garage ,and EV charging station. From the hand-carved Tibetan gates to the tranquil pond and water feature, every detail of Storybook reflects a reverence for Sarasota’s natural beauty and a deep sense of peace and privacy. This is more than a home — it’s a place to breathe, reflect, and feel fully connected to the world around you.

Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)

Listing Agent: Dianne Anderson (941-350-3513)

Remarks: One or more photo(s) has been virtually staged. Experience the art of beachfront living in this exceptional 4-bedroom, 4-bath Gulf-front residence, where sweeping water views and unforgettable sunsets take center stage. Spanning three thoughtfully designed levels, this coastal retreat offers a rare blend of refined comfort and effortless elegance. Walls of glass frame the Gulf from nearly every vantage point, filling the home with natural light and showcasing breathtaking vistas that evolve throughout the day. A private elevator provides seamless access to all floors, while expansive living spaces invite both relaxed everyday living and refined entertaining. Recent enhancements—including impact windows and sliders, four updated HVAC systems, and a new water system—ensure peace of mind while complementing the home’s modern coastal aesthetic. The guest bathrooms have also been tastefully updated with fresh, contemporary finishes, offering a polished and comfortable experience for family and visitors alike. Step outside to multiple outdoor living areas designed to capture the essence of coastal living. The rooftop terrace is a true showpiece, complete with a private jacuzzi—an idyllic setting to unwind under the stars or take in spectacular sunset views over the Gulf. With direct beach access just beyond your door, every day begins and ends with the soothing rhythm of the waves. Perfectly positioned on Blind Pass Road, this home offers both privacy and proximity to the charm of Siesta Key’s vibrant coastal lifestyle. This is more than a home—it’s a front-row seat to the Gulf, where every day feels like a getaway.

Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)

Listing Agent: Holly Pascarella, Pa (941-225-3218)

Remarks: Luxury living with spectacular sunset waterfront views in the gated community of Phillippi Landings, offering boating access and a prime Sarasota location just minutes from Siesta Key Beach and downtown. This sixth-floor residence overlooks Phillippi Creek with glimpses of the Intracoastal Waterway and a peek of the Gulf from the private screened balcony. The 2-bedroom, 2-bath plus den floor plan features 10-foot ceilings, crown molding, and numerous upgrades including a newer A/C system, LG refrigerator, LG washer and dryer, KitchenAid dishwasher, Lumens ceiling fans, and upgraded lighting. The kitchen offers granite countertops, wood cabinetry, and stainless steel appliances, opening to the living area and screened balcony through 8-foot sliding doors for seamless indoor-outdoor living for relaxing or entertaining. The primary suite features wood flooring, two walk-in closets, and a spacious bath with dual vanities, garden tub, and walk-in shower. Residents enjoy resort-style amenities including a heated waterfront pool and spa, fitness center, clubhouse, kayak launch, dog park, and scenic boardwalk. High-end turnkey furnishings option available.

Listing is courtesy of: ALBERT WOOSTER & COMPANY (941-350-1220)

Listing Agent: Albert Wooster (941-350-1220)

Remarks: PRICE IMPROVEMENT OF $20.000!! Turnkey coastal living in the desirable mid-rise tower at Peppertree Bay on Siesta Key. This sought-after split-plan residence offers bright open living spaces, exceptional privacy, and the convenience of effortless island living with resort-style Gulf-to-Bay amenities just moments from world-famous Siesta Beach. Offered fully turnkey furnished, this beautifully maintained two-bedroom, two-bath residence is ready for immediate enjoyment as a primary residence, seasonal retreat, or investment property. The split-bedroom layout provides privacy for owners and guests, while the open living and dining areas create a comfortable space for everyday living and entertaining. A feature seldom found in these units is the dedicated laundry room with a utility sink, adding both convenience and functionality. The residence also includes elevator access, covered parking, and generous storage. Peppertree Bay is one of Siesta Key’s most sought-after Gulf-to-Bay communities, offering private beach access to the powdery quartz sands of Siesta Beach, two heated pools, tennis and pickleball courts, a fitness center, clubhouse, fishing pier, and beautifully maintained tropical grounds. Ideally located just minutes from Siesta Village dining, shopping, and entertainment, this residence offers the best of relaxed island living.

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

Listing Agent: Renee Nadiv (941-299-4242)

Remarks: Located directly across the street from world-famous Siesta Key Beach—recently ranked the #1 Beach in the United States and among the top beaches in the world— this residence offers exceptional convenience and effortless access to the sand. Simply walk to the beach in approximately five minutes—no driving, no searching for parking, just easy coastal living. Enjoy morning walks and evening sunsets on Siesta Key Beach just steps away. This 2-bedroom, 2 full bath residence offers approximately 940 square feet of comfortable living space with an open layout designed for relaxed island living. The updated kitchen features wood cabinetry, granite countertops, and stainless steel appliances, flowing seamlessly into the dining and living areas. Tile flooring throughout provides durability and easy maintenance, while the split-bedroom floor plan allows for privacy between residents and guests. One of the largest 2-bedroom, 2 full bath floor plans in the community, competitively priced at $593,000. Weekly rentals are permitted, offering outstanding flexibility for both personal use and income potential. Onsite property management is available, making guest coordination and rental operations easy and convenient. Covered parking is included, along with ample guest parking. La Siesta residents enjoy access to a heated pool, fitness room, clubhouse, and beautifully maintained grounds. Located just minutes from Siesta Key Village’s restaurants, shopping, and entertainment, this property offers the ideal balance of relaxation and accessibility. Whether you’re searching for a personal beach retreat, seasonal residence, or an income-producing investment, this location delivers the lifestyle buyers and vacationers come to Siesta Key to enjoy.

Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)

Listing Agent: Lisa Garcia (941-266-9060)

Remarks: One or more photo(s) has been virtually staged. In Sarasota's desired West of Trail enclave of Cherokee Park, 1655 South Drive, masterfully designed three-story estate where thoughtful architecture meets effortless luxury. Positioned on a homesite that is not in a Special Flood Hazard Area and enhanced with full home hurricane-impact glass and a whole-home generator, this residence offers the rare combination of refinement and peace of mind. Spanning 6,355+ square feet, the home features five bedrooms, five full baths and four half baths, with a layout tailored for grand entertaining and everyday ease. A rear three-car garage, accessed discreetly from South Lodge Drive, preserves the home's striking street presence. Inside, the main level unfolds into a wide-open living experience with a great room with wet bar, formal dining, and a showpiece chef's kitchen outfitted with Wolf dual-oven six-burner range, dual side by side 36” Sub-Zero Over-and-Under Refrigerator/Freezers, a Wolf microwave drawer, a Wolf warming drawer, and built-in Miele espresso machine. The first-floor primary suite is a private retreat, complete with an in-home gym, a spa-inspired bath and dual custom-fitted closets. A beautifully appointed guest suite (fifth bedroom) with en-suite bath also anchors the main level. Access to the upper floors is seamless via a dramatic staircase with custom wrought-iron railings or the private elevator. Upstairs, three additional en-suite bedrooms include custom walk-in closets, one thoughtfully designed with built-in bunk beds, plus a bonus club room with built-in desks and additional laundry for added convenience. Outdoors, the property transforms into a walled and gated resort-style oasis featuring a gas-heated saltwater pool with sun shelf and spa, and an artificial turf lounge/play area. A screened entertainment lounge with a convenient half pool bath connects to a full outdoor kitchen with sink, TV and gas grill, all complemented by a pergola and a mosquito misting system, ideal for Sarasota's seasons. Above the garage, a spectacular casita-style retreat, accessible by the home’s second private interior elevator or exterior spiral staircase, elevates entertaining to an entirely new level with a 2,000-bottle refrigerated wine room, a fully equipped wet bar, mini- fridge, clear ice maker, and dishwasher. Go onto the covered terrace with a gas fireplace, then unwind on the third floor in the private, pool-like infinity-edge spa, an experience that feels equal parts boutique resort and private club. Ideally in walking distance to A-rated Southside Elementary School, Southside Village, Sarasota Memorial Hospital, downtown Sarasota and short drive to the world-famous sands of Siesta Key Beach, this is a rare opportunity to own a bespoke residence in one of Sarasota's treasured neighborhoods.

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

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

Remarks: TOP-FLOOR END UNIT WITH WATER VIEWS! Experience the ultimate 'plug-and-play' Florida lifestyle in this charming, turnkey-furnished retreat. Perfectly positioned in a maintenance-free, two-story building, this residence overlooks a peaceful pond and is ready for immediate move-in or rental. THE TURNKEY ADVANTAGE: Sold fully furnished, including a 50” Samsung Smart TV (Living Room) and a 43” Samsung Smart TV (Bedroom). Just bring your suitcase! PEACE OF MIND: Major updates are done—New Roof (2024), Range (2025), and HVAC/Water Heater (2018). Features include a private balcony with storage, in-unit stacked washer/dryer, and a pet-friendly policy for both cats and dogs. LOCATION: Just 4 miles to Siesta Key Beach. Enjoy the heated community pool and fitness center. Whether you’re looking for a seasonal escape or a rental-ready investment, this is the best value in 34231. View the 3D Virtual Matterport Tour by clicking on the link.

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

Listing Agent: Tessa Robbins, Pa (941-374-1345)

Remarks: Turnkey Furnished residence at Island Reef with two bedrooms and two baths. Laundry in residence. Furnished! Carport! island Reef is a serene waterfront community, one of the few gulf to Bay Community that offers many desirable amenities including: Beach, Boat Docks (lifts allowed), Two lit Tennis Courts, Pickleball, 2 Fitness Rooms, Kayak storage, Library, Billiards, Game room, Clubhouse, two Heated Pools, and Gas grills. PET FRIENDLY! Tropical Gardens add to the appeal of Island Reef and this wonderful community is close to two of Siesta Key's popular restaurants. Complimentary trolley to Siesta Beach, Siesta Village for dining, shopping, ice cream, mini donuts, cut brunch spots and dancing and live music every night of the week.

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

Listing Agent: Marlene Marshall (941-539-8850)