Homes for Sale Near Brookside Middle in Sarasota - 505 homes

Remarks: Perched on the 6th floor with sweeping, unobstructed western views of the Gulf and world famous Crescent Beach, this spectacular Siesta Key condo delivers front row sunsets and frequent dolphin sightings, stretching from Point of Rocks to north Siesta Key. Ideally positioned above the gulf front pool and spa, this partially furnished island retreat is move in ready and features a full length enclosed balcony for added living space, along with impact windows and doors for peace of mind. Located in Horizons West, a coveted gulf to bay resort community spanning over 7 lushly landscaped acres, residents enjoy 300 feet of deeded private beach with cabanas, a beachside pool and spa, grilling areas, a second pool by the clubhouse, and a private Intracoastal Waterway park with day dock perfect for kayaking, paddleboarding, fishing, or relaxing among the mangroves. Conveniently access Siesta Key Village dining, shopping, and entertainment via the free island trolley and embrace the ultimate carefree coastal lifestyle. Come see what Island Life is all about.

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

Listing Agent: Suki Scollo (941-587-2289)

Remarks: **This is The One!** Prime Sarasota location just minutes to Siesta Key Beach, Downtown Sarasota, and more! This property offers strong potential as a primary residence, seasonal home, or investment opportunity. **NEW Roof in 2021** Functional layout with solid bones and opportunity to update or customize to maximize value. Private outdoor space and convenient access to shopping, dining, medical facilities, and I-75 add to the appeal. Ideal for buyers looking to capitalize on location and long-term upside in a highly desirable area. **NO HOA or Deed Restrictions** The Florida room provides the perfect spot to enjoy your morning coffee or unwind in the evening, and it opens to a spacious outdoor area—ideal for taking full advantage of Florida’s beautiful weather year-round. This property offers a versatile bonus space currently set up as a workshop **Potential to turn bonus space into living space/in-law suite with private entrance**, along with an additional climate-controlled room perfect for a home gym or flex space. Equipped with a 2-car attached garage PLUS an extra driveway on the side **Ample room for storing a Boat, Trailer, Lawn equipment, or other recreational vehicles.** Enjoy the freedom to truly make the space your own with endless possibilities. In addition, enjoy tons of storage space for all your holiday decorations and any additional items you may need to tuck away. Don't miss out on this incredible property - Reach out to schedule your private tour today!

Listing is courtesy of: HARRY ROBBINS ASSOC INC (941-924-8346)

Listing Agent: Ryan Miller (941-954-6925)

Remarks: Experience the pinnacle of island living in this 9th-floor, west-facing penthouse offering sweeping, unobstructed Gulf and Crescent Beach views from Point of Rocks to iconic Siesta Beach, where nightly sunsets paint the sky. Perfectly positioned above Siesta Key’s crystal-white sands, this spacious residence features 2 bedrooms and 2 baths with the rare opportunity to expand to a third bedroom and bath, allowing you to customize your coastal retreat. Highlights include a full laundry room, impact-rated windows, tankless water heater, dual A/C systems, and a coveted private 2-car garage with direct lobby access—one of only four in the community. Located in the prestigious Horizons West, a gated gulf-to-bay enclave spanning more than seven lush acres, residents enjoy 300 feet of private beachfront, beach cabanas, a Gulf-front pool and spa, grilling areas, a bayside pool and clubhouse, and a private intracoastal park with day dock, kayak launch, and serene mangrove setting. With SIRS and Milestone inspections complete and new landscaping throughout, this exceptional penthouse delivers luxury, privacy, and the ultimate Siesta Key beachfront lifestyle.

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

Listing Agent: Suki Scollo (941-587-2289)

Remarks: Welcome to this beautifully updated 3-bedroom, 2-bath pool home in the highly desirable Gulf Gate Woods community of Sarasota—where major upgrades have already been completed, offering true peace of mind and effortless Florida living. Freshly painted with new carpet in the bedrooms, the home feels clean, bright, and inviting. A thoughtful layout provides a comfortable flow, complemented by a blend of ceramic tile and hardwood flooring. The kitchen and dining areas are both functional and welcoming—perfect for everyday living or entertaining. Significant recent improvements include a 2026 tile roof with transferable warranty, 2026 Lennox HVAC system, and a 2026 pool pump, giving buyers confidence in the home’s major systems. Additional enhancements such as a 2025 impact-rated front door, full home replumbing, and new gutters further add to the home’s value and durability. Step outside to your private screened lanai and pool area, where the pool deck and cage have been refurbished and upgraded with high wind impact screens—creating the ideal setting to relax and enjoy year-round outdoor living. The spacious primary suite features a private ensuite bath with a separate shower and a walk-in closet. Two additional bedrooms provide flexibility for guests, a home office, or family needs. A 2-car garage and dedicated laundry room complete the home. Situated in a well-established community with an optional HOA and zoned for A-rated schools, this property is just minutes from shopping, dining, and Sarasota’s world-renowned beaches. Furniture is available for purchase, making this a truly move-in ready opportunity.

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

Listing Agent: Brian Wood (941-928-8408)

Remarks: Welcome to this charming 1500+ sq ft 2 Bedroom 1 Bath home in a quiet neighborhood close to shopping, the famous Siesta Key Beaches, gorgeous downtown Sarasota, and very fine dining. Inside the home, there is an open layout with tile flooring and natural light throughout, that gives a warm and welcome feeling. The front living room is a large space with a big bay window. The expanded and bright kitchen is adorned by layered brick on the wall, two newly replaced skylights, and most of all, ample wood cabinets and breakfast bar for convenience. The featured dining area is bright and have beautiful built in shelves for your decorations and is ready for hosting dinner parties. In the rear, you will find a family room where you can relax and view the majestic oak tree in your big backyard. There are two bedrooms on the west end of the house, with windowed natural light plus extra-large closets. The spacious one bathroom has two sinks and a tub with shower. There is a bonus utility room with washer, dryer, sink, walk in closet, and office space. From the family room, step through double french doors to the spacious roofed and screened lanai to enjoy breezes and urban wildlife. You will love the expansive deep lot, with plenty of room to possibly build a cottage , swimming pool and tropical gardens. Bring your dogs or pets, the yard is fenced in. The home has many upgrades including new roof, HVAC, and hurricane windows. Come see and imagine the Florida lifestyle in beautiful Sarasota.

Listing is courtesy of: MS REALTY MICKEY SCHWEITZER & ASSOCIATES LLC (941-914-2460)

Listing Agent: Grace Bergeron (941-586-3279)

Remarks: Find your sanctuary in this exquisite Allegra custom home, ideally located on one of the few non-throughfare streets in the highly coveted West of the Trail neighborhood. Serene and understated from the outside, the home opens to a breathtaking entry that reveals an extraordinary Great Room featuring soaring 21-foot beamed ceilings, a dramatic windowed rotunda, and an open-concept design bathed in natural light. Oversized 10-foot doors frame every room, while hurricane-impact sliding glass doors seamlessly connect the interior to a resort-style outdoor oasis. The expansive pool deck showcases a stunning lighted fountain spilling from the spa into the oversized pool, a rainfall pergola, and lush tropical landscaping surrounded by a six-foot privacy fence—creating the ultimate setting for both relaxation and entertaining. Built with the signature craftsmanship of Allegra Homes, the residence features exceptional custom millwork, striking feature walls, designer lighting, and distinctive ceiling details throughout. Spanning 3,582 square feet, this thoughtfully designed home offers four spacious bedrooms, three luxurious bathrooms, a private den/office with a turret ceiling, and a versatile bonus room. The gourmet kitchen—one of Allegra’s most beloved layouts—is a true culinary showpiece, appointed with Sub-Zero and Wolf professional-series stainless steel appliances, including a five-burner natural gas cooktop, a second Sub-Zero beverage refrigerator, custom luxury cabinetry, rich 3cm granite countertops, and a glass tile backsplash with hidden electrical outlets Adjacent to the kitchen, the elegant dining room features a dramatic aquarium glass window overlooking the pool and gardens, along with a built-in buffet accented by a mirrored feature wall. The home’s split floor plan provides exceptional privacy. The serene primary suite is a private retreat, offering a spa-inspired bath with a walk-through shower, dual vanities, and a private water closet. A custom walk-in closet features built-in shelving, drawers, and a hallway dressing mirror. The bedroom is highlighted by an intricate custom ceiling design, designer lighting, and private access to the pool deck. On the opposite side of the first floor, you’ll find a built-in desk alcove, a spacious laundry room, a secondary bedroom with a walk-in closet, a full hall bath, and the bonus room with disappearing sliding glass doors that open to the screened pool area. The first level features rich porcelain wood-style flooring, while the second level is comfortably carpeted and hosts the third and fourth bedrooms, along with a media closet and additional HVAC storage. Bahama shutters and custom blinds complete the bedrooms and bathrooms. Situated on a 0.28-acre elevated lot, built above the flood plain in 2015, this exceptional residence offers privacy, luxury, and an unbeatable central location. Just minutes away are Sarasota Memorial Hospital, Southside Village, and top-rated Southside Elementary, with Siesta Key Beach, downtown Sarasota, Westfield Siesta Key Mall, and St. Armands Circle only a short drive away. This remarkable property may be purchased turnkey furnished, including original artwork, bronze sculptures, designer furnishings, and custom rugs, available under a separate bill of sale. Schedule your private showing today. Proof of funds required with all offers.

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

Listing Agent: Jill Berg (941-315-1199)

Remarks: Experience the pinnacle of waterfront luxury on Siesta Key’s prestigious Grand Canal. This meticulously reimagined residence at 4938 Commonwealth Drive offers a rare blend of modern sophistication, structural integrity, and complete peace of mind. Extensively transformed both structurally and aesthetically, the home welcomes you into an expansive open-concept design filled with natural light. The newly expanded kitchen serves as the heart of the home, offering abundant cabinetry and storage, a double oven, generous pantry storage, striking custom beam detail, an open breakfast bar, and direct access to the wraparound decking—creating seamless indoor-outdoor living and effortless entertaining. A stylish powder room has also been thoughtfully added. New hurricane-impact windows and sliding glass doors frame the interiors, while designer flooring flows beautifully throughout both levels. Major system upgrades elevate the home’s value and efficiency, including a brand-new roof and a comprehensive solar power system with battery storage. A fresh, contemporary interior palette enhances the clean architectural lines and airy coastal feel. The lower level adds over 1,300 square feet of legal non-conforming living space with its own private entry, garage access, and elevator connection to the main living areas, leading directly to the pool deck. Redesigned for modern functionality, this space features a spacious family entertainment area, custom bar, and an additional guest suite with a walk-in closet and full bath—ideal for extended family, guests, or a private retreat. Outdoor living is equally impressive. The private backyard sanctuary showcases a heated pool and spa with a new heater and filtration system, sleek updated decking, professional landscaping, and premium artificial turf for effortless maintenance. For the boating enthusiast, the deep-water dock and boat lift provide direct access to the Intracoastal Waterway and open waters of Sarasota Bay, delivering the ultimate waterfront lifestyle.

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

Listing Agent: Maurice Menager (941-238-8119)

Remarks: Experience the best of waterfront living in this beautifully updated and fully furnished second-floor condo in the highly sought-after Siesta Harbor community. This TURNKEY 2-bedroom, 2-bath residence offers stunning canal and marina views and a prime location just steps from direct beach access across the street through Crescent Arms. Immaculately maintained and move-in ready, the condo features an enclosed lanai with horizontal sliding windows, tasteful furnishings, and thoughtful updates throughout for comfort and relaxation. The spacious open-concept living and dining areas flow seamlessly into a modern kitchen showcasing white cabinetry, quartz countertops, stainless steel appliances, and ample storage. The primary suite includes a walk-in closet and a stand-up shower, while the enclosed lanai provides the perfect spot to enjoy morning coffee or evening cocktails year-round, with dolphins frequently seen playing in the marina. Siesta Harbor is a vibrant 55+ waterfront boating community situated on its own canal and the main waterway of the Intracoastal Waterway. Boat slips may be available for vessels up to 30' (check with the office for availability). Residents enjoy resort-style activities, and amenities including a heated pool, outdoor jacuzzi and shower, indoor sauna, fitness room, shuffleboard court, fishing pier with seating on the ICW, and a beautifully renovated clubhouse with full kitchen, outstanding library, barbecue area with grills, and a full calendar of social activities. Additional highlights include FOB-accessed private beach access, FREE laundry on the 2nd, 3rd, and 4th floors, one designated covered carport parking space, ample guest parking, covered parking, an on-site manager, lush tropical landscaping, and a new roof (2025). Ideally located near the South Bridge, this community offers easy on-and-off access to the Key, is within short distance to restaurants and shops, and has the free Siesta Key trolley stopping right in front of the complex for easy access to Siesta Key Public Beach and Siesta Key Village. Whether you're watching boats drift by on the Intracoastal, crossing the street for unforgettable sunsets, or enjoying the active social lifestyle, this property is perfect as a vacation retreat, full-time residence, or investment opportunity. You deserve paradise!

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

Listing Agent: David Anthony (941-786-4282)

Remarks: One or more photo(s) has been virtually staged. Great price for walled-in pool home in PRIME WEST OF TRAIL location, just a few blocks to Southside Village popular shops and restaurants and 1 block to Sarasota Memorial Hospital. The home was remodeled in 1996 and 2000 with vaulted ceilings, newer bathrooms and kitchen, split bedroom floor plan, pool (built in 2003 and Pebbletec resurfacing in 2026), interior laundry room and 1 car garage. Tile or wood floors throughout. Property re-piped in 2024, a/c 2019. Perfect for your residence or an easy investment property with weekly or monthly rentals allowed. Rental estimates range from $6k - 7.5k monthly depending on annual or weekly rental. Very limited rental availability in the area.

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

Listing Agent: Barbara May (404-822-9264)

Remarks: Welcome to 1959 Wisteria Street – a beautiful New Construction Single Story home, West of the Trail, that your clients will love! This just-completed modern coastal single story home is located West of the Trail in preferred Flood Zone X, offering elevated storm protection and convenient access to Southside Village, Downtown Sarasota and Siesta Key beaches. Designed and built with Majestik Homes' signature strength and style, this 3 bedroom plus office, 4 bath home blends architectural elegance with energy efficiency and storm-ready construction. You will be awestruck as you open the home’s large glass-paneled double doors and step into a spacious foyer that flows seamlessly into an expansive great room filled with natural light and a striking entertainment wall — perfect for relaxed living and stylish entertaining. Panoramic sliding glass doors open to a private backyard oasis featuring a sparkling pool and spa, and a fully appointed outdoor BBQ area designed for effortless Florida entertaining. The chef’s kitchen features high-end gas appliances, and the dining room is ideal for intimate dinners and larger gatherings alike. The Primary Suite is spacious and luxurious with its own private lanai. The spa-inspired primary bath offers both an indoor shower and a private outdoor shower for a true resort-style experience. Bedroom 3 includes an en-suite bath. Situated on a generous homesite with large side yards and enhanced privacy, the property is complemented by a circular driveway and an oversized 3-car garage — providing ample space for guests, storage, and everyday functionality. Beautifully staged and thoughtfully designed, this home showcases artwork from some of the local area’s most inspiring artists. Easy to show — you won’t want to miss this exceptional opportunity.

Listing is courtesy of: MAJESTIK REALTY, INC (941-363-6080)

Listing Agent: Michael Hankin (941-504-4337)

Remarks: Experience the ultimate Siesta Key beach get-away in your TURNKEY FURNISHED, west-facing condo at Horizons West and just steps from your private beach with plenty of beach chairs and five sun cabanas. Enjoy the crystal sands of Crescent Beach where the sand is always cool and you’ll never miss a sunset. This spacious 1-bedroom retreat boasts over 1,000 sq. ft. and has tiered ceilings up to 9 ½ feet. The west facing wall of oversized 6-foot-high impact windows frame breathtaking panoramic Gulf, beach, resort pool and sunsets sunset views, including dolphin sightings. Perched above the lobby and mezzanine, use the elevator to enter this bright and cheerful end-unit with west and south facing windows in the living room. Enjoy an open, airy floor plan with a designer kitchen featuring stone countertops, stainless appliances, and a breakfast bar. The generously sized bedroom has south and east facing windows and an en-suite bathroom with a beautifully tiled walk-in shower. Resort-style amenities abound: 300 ft. of private beach, two pools, spa, cabanas, grills, and a bayside park with day dock. This unit comes with private carport storage for all your beach toys. Hop on the free Siesta Key trolley for world-class dining and shopping. Come see why Siesta Key is ranked the #1 Beach in the USA and #4 in the world—your piece of paradise awaits!

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

Listing Agent: Suki Scollo (941-587-2289)

Remarks: Full west-facing gulf and beach views from this exquisitely designed 3-bedroom condo on Siesta Key’s famed Crescent Beach. This highly desirable end-unit has views from Point of Rocks to the north end of Siesta Key Beach. Never miss a sunset from this turnkey-furnished, move in ready home. No expense was spared in creating this seaside oasis. The original space was reconfigured to add a 3rd bedroom, open the kitchen, and enclose the 30-foot balcony. Slide open the walls of west-facing impact windows bring in the sounds of the beach. The primary bedroom has a wall of accordion glass the folds open to expand the open concept layout. Continuous luxury vinyl flooring throughout the unit creates a seamless transition between spaces. The kitchen has bar seating for 7, an induction stovetop, quartz countertops, and a high-end mosaic backsplash. Across from the kitchen is the dry bar with built-in wine refrigerator and separate ice maker. There is crown molding, dimmable recessed lighting, 5 ½” baseboards, an in-ceiling speaker system throughout the home. The primary bedroom has dual walk-in closets. Updated bathrooms include walk-in showers and stone countertops. This once-in-a-lifetime property is located in Horizons West, a gulf-to-bay community with 300 feet of private beach access and over 7-acres of lush grounds. There are 2 heated pools-one with beach views, a gulf-side spa, beach cabanas and beachside grilling areas. The grounds include an intracoastal waterway park with day dock and a grilling area that is perfect for manatee watching or launching a kayak. Siesta Key’s free island trolley can deliver you to exceptional dining, shopping and entertainment. Welcome home to Siesta Key.

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

Listing Agent: Suki Scollo (941-587-2289)

Remarks: Have you ever dreamed of living on the beach??? Your chance has arrived! Step into coastal paradise at this turnkey-furnished Siesta Key residence, perfectly situated on the tranquil southern end of the island in the coveted Tortuga community. Residents enjoy a wide range of resort-style amenities, including a heated indoor/outdoor pool, sauna, tennis and pickleball, shuffleboard, and a fishing pier. And, the laundry room is just outside the front door! The community has recently completed major improvements, including a new roof, freshly painted buildings, and a refreshed pool, with all assessments fully paid. The updated clubhouse features a full kitchen and dining area and may be reserved for private gatherings. Impact-resistant windows and doors offer peace of mind. With direct deeded beach access, resort-style amenities, and optional boat slip access ($300/year when available) on the Intracoastal Waterway just across the street, this is island living at its finest. This 800-square-foot condo boasts an open, light-filled floor plan with wood-like tile flooring, crown molding, and a spacious living and dining area that flows effortlessly onto a screened balcony overlooking lush tropical landscaping—perfect for morning coffee or sunset cocktails. The kitchen is a showstopper, featuring quartz countertops, a breakfast bar, and modern appliances, creating a seamless space for entertaining friends and family. The primary suite is a true retreat, complete with a walk-in closet and an en suite bath with dual sinks and granite surfaces. Located on the second floor with elevator access, convenience is key, including nearby shared laundry facilities. Whether you’re seeking a year-round home or seasonal escape, this residence embodies the relaxed sophistication of island life while keeping you just minutes from the world-famous quartz sands of Siesta Beach, the charming boutiques and dining of Siesta Key Village, and the vibrant arts and culture of downtown Sarasota. Coastal living doesn’t get any better than this—your slice of paradise is waiting!

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

Listing Agent: Roberta Tengerdy, Pa (941-321-2292)

Remarks: Welcome to Ashton Pines, a community of 11 homes conveniently located to everything Sarasota has to offer. The updates in this home are dramatic featuring an open floor plan with volume ceilings in the great room. The expansive kitchen has upgraded cabinets & appliances with marble(yes, MARBLE) counter tops. There is a spacious breakfast area. The expansive primary bedroom has volume ceilings and a large half round window for amazing natural light. In addition to a 7 x 5 walk in closet, there is an upgraded private bath. The oversize shower stall has 2 shower heads, one a rain shower. There is a private courtyard with a sliding glass door that brightens the whole room. The split plan has two bedrooms on the north side of the home along with the main bath. The kitchen, living room, & primary bedroom all have sliders to access the screened lanai and rear yard. The laundry room offers additional storage and access to the 2 car garage. The access to Siesta Beach(2 miles), I75(5 miles),and any shopping or restaurants on Clark Road & Tamiami Trail is available with a quick drive. This is a great location for a primary home, secondary home, or an investment property.

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

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

Remarks: The Epitome of Refined Coastal Luxury in Hudson Bayou: this custom-built Edgewater residence offers a pristine living space crafted with meticulous attention to detail and luxury throughout. Its sleek façade invites you into a world where modern elegance meets tropical serenity. Inside, sunlight pours through expansive windows onto wide-plank Spanish White Oak floors. The open-concept living area flows effortlessly beneath soaring ceilings and modern architectural lines. At the heart of the home, the gourmet chef’s kitchen features Thermador appliances hidden behind sleek cabinetry, quartz countertops, and a dramatic waterfall island designed for culinary artistry and entertaining. The layout blends open gathering areas with private retreats. The main-level Owner’s Retreat offers an unparalleled sense of serenity, with a spa-inspired en-suite featuring a lavish rain shower, a freestanding soaking tub, and designer fixtures. Upstairs, a second primary suite ensures family and guests enjoy equal comfort and privacy – complete with a balcony – a tranquil haven for morning coffee or evening breezes. The home’s dedicated spa-inspired wellness area, with a private sauna and cold plunge, offers an immersive environment for restorative living – the ultimate escape for refined relaxation and wellness. Additionally, a club room with direct outdoor access offers flexible space – an executive office by day and a media lounge by night. The home is also equipped with a RO system in the kitchen and a whole-house water filtration system for pure water throughout. Resort-Style Outdoor Living: step outside into a luxurious oasis that feels like a private resort. The expansive screened lanai spans the back of the home, ensuring insect-free comfort while framing views of lush palm trees and the heated saltwater pool. Multiple lounge areas and a covered alfresco dining space plenty of room for relaxation and entertaining. Fire up the grill for poolside BBQs, host a soirée, or simply unwind with a sunset cocktail. The resort-style pool offers a private island-style escape, surrounded by tropical greenery for seclusion. Whether soaking up the sun on a chaise or chatting in the shade, this outdoor haven makes every day feel like a vacation. Prime Location & Lifestyle: nestled on a quiet dead-end street in prestigious Hudson Bayou — a highly sought-after West of Trail/West of Osprey enclave with its own quaint Pomelo Park — this home offers peaceful privacy while being just moments from vibrant downtown Sarasota. In this golf cart-friendly neighborhood, you’re a short ride from Marie Selby Botanical Gardens, Marina Jack and Bayfront Park. Downtown Sarasota’s boutique shopping, art galleries, theaters, and fine dining are all within a mile, as is the charming Southside Village — home to the iconic Morton’s Gourmet Market and various restaurants and bars. Sarasota Memorial Hospital is also less than a mile away. The property sits in Zone X (not in a flood zone), meaning no flood insurance is required. It is also zoned for the coveted Southside School District, so top-rated schools are within easy reach. This property embodies the ultimate coastal lifestyle, perfect for cherished family memories or substantial rental income, thanks to its short-term rental zoning within Sarasota’s city limits. This is the ultimate retreat for the discerning buyer seeking sophistication and relaxation – a rare opportunity where privacy, luxury, and location converge.

Listing is courtesy of: AMY ROBINSON REAL ESTATE LLC (941-346-7000)

Listing Agent: Amy Robinson (941-928-2044)

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: Under Construction. Experience refined luxury living at Bath & Racquet Residences, where modern elegance meets Sarasota’s storied legacy. This thoughtfully designed two-bedroom, 2.5-bath loft-style residence features floor-to-ceiling windows, custom Italian cabinetry, quartz countertops, premium Bosch appliances, and an expansive outdoor patio with built-in planters—perfect for seamless indoor-outdoor living. Ideally situated in a prime location near the club. Beyond your doorstep, enjoy an unparalleled collection of resort-style amenities. The community and club feature a private pool, expansive two-acre park, dog park, playground, and a scenic 1-kilometer walking trail—ideal for an active outdoor lifestyle. Sports and wellness enthusiasts will appreciate 13 tennis courts, 2ipickleball courts, 4 padel courts, a resort-style club pool, on-site restaurant, state-of-the-art fitness center, and a full-service wellness spa. Located just 4 miles from the world-famous Siesta Key beaches and 3 miles from vibrant Downtown Sarasota, this address offers the perfect blend of luxury, convenience, and coastal sophistication. Bath & Racquet Residences presents a unique opportunity for both full-time residents and investors, with short-term rentals permitted (7-night minimum), offering flexibility and income potential. Under the guidance of Tommy Haas, former World No. 2 and official club ambassador, this iconic redevelopment reimagines the historic Bath & Racquet Club, originally founded in 1969. Once the home court of tennis legends such as Chris Evert and Martina Navratilova, the property now enters a new era—honoring its rich heritage while embracing modern elegance, wellness, and active living. Designed by the acclaimed Halflants + Pichette Architects, Bath & Racquet Residences and Club presents 256 luxury condominiums with low HOA fees.

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

Listing Agent: Cari Miller (203-722-4509)

Remarks: Live in one of the most desirable Sarasota neighborhoods! This home has 2 nice sized bedrooms and a third room that can be a sunroom, office, or interior in-law suite/studio with its own bathroom, kitchen space, closet, and private entrance from the back of the house. This cozy home features a kitchen nook and comfortable sitting area to relax and unwind. Upgrades include remodeled kitchen, newer roof (2018), Granite vanity top and sink with brushed nickel faucets (2020), water heater (2025), upgraded light fixtures (2025) and many other upgrades throughout this beautiful home. Enjoy your morning coffee from the beautiful front patio or relax on the back patio. Backyard has a 2-car carport and storage sheds. The location is ideal as it is close to shopping and restaurants as well as minutes to downtown Sarasota and world-famous Siesta Key Beach & other local beaches. Schedule an appointment to see this beautiful home today! RV parking available as well as zoned for multi-family if desired.

Listing is courtesy of: CHROME REALTY LLC (941-363-6300)

Listing Agent: Marni Hayden (941-809-5044)

Remarks: The highly-acclaimed team of professionals at Allegra Homes has yet again created a vision of luxury, elegance and simplistic functionality. A dynamic 4,224 sq. ft. open layout is rich in gorgeous details everywhere you turn. Feast your eyes on the “St. Michael,” a two-story beauty with stunning curb appeal and exciting interiors thoughtfully designed for grand-scale living. In addition to 4 bedrooms, there’s also a separate 254 sq. ft. casita ideally suited for in-laws or guests wanting to enjoy the fantastic Florida ambiance just a little longer. The extended foyer and great room feature an amazing 21-ft ceiling and invite you into a fascinating space with see-thru views out to the magnificent outdoors. Step into the heart of the home, where the great room exudes warmth and sophistication. A wood-beamed ceiling adds character and warmth, while clerestory windows flood the space with natural light, creating an inviting and airy ambiance. Triple sliders seamlessly connect the indoors to the covered poolside lanai. In the family room, a stunning stone-faced center wall serves as the focal point, flanked by built-in shelving with elegant lighting. The consummate chef will delight in the variety of accoutrements offered in this delectable space honed to perfection. A large stone-topped island easily seats 5 and the premium appliance package encompasses a 36” Wolf gas induction cooktop, a 42” Sub-Zero fridge, a Wolf oven with matching drop-down microwave, an ASKO dishwasher, a Sub-Zero wine cooler, and adequate counter and storage space including a pantry. Adding stylish flair to the dining room is a built-in buffet with full mirrored wall and wide windows overlooking the tropical pool setting. A separate dry bar with pass-thru is convenient to both the great room and kitchen for ease of serving family and friends. Overlooking the pool is a bonus room with a pool bath and wall of pocketing sliders opening wide to a covered 545 sq. ft. outdoor oasis with tongue-and-groove ceiling, nicely equipped summer kitchen, and abundant room for both dining and lounging. The pavered lanai is enclosed with ClearView screening and includes a 25’x19’ heated pool with 6 stepping pads, spill over spa, sun shelf, LED bubbler, salt conversion generator and Pebble Tec finish. The owner’s wing, with an adjacent study, may become your most prized room of the home with its drop tray ceiling, spacious seating area, soaking tub inside an exquisite large glass shower, separate dual vanities and water closet. An additional bonus room with wet bar, two bedrooms and a bath are located upstairs. Other honorable mentions include a 3-car garage with epoxy floor, tankless gas water heater, 10-ft ceilings, modern staircase with floating steps, recessed lighting, crown molding, brick paver drive and walkway, 8’ interior solid core doors, professionally landscaped, and irrigation system. Poised on over a 1/3 acre lot in prestigious Harbor Acres with a sought-after central location near the arts, entertainment, dining, shopping, beaches, boating, golf and other year-round adventures. For families with elementary school-age children, top-ranked Southside School celebrates 120 years of excellence in academic achievement. This stately new residence has been masterfully crafted inside and out, and will add a sense of pride and joy to an already perfect lifestyle.

Listing is courtesy of: GRECO REAL ESTATE (941-685-0449)

Listing Agent: Karen Greco (941-504-6927)

Remarks: Luxury Waterfront Living Now Priced to Move Welcome to 4508 Woodside Rd, a true boater’s paradise on Siesta Key offering privacy, deep-water access, and refined coastal living. Positioned on one of the island’s deepest canals, this property provides quick access to the Intracoastal and Sarasota Bay, with 95 feet of waterfront and a 75-foot dock designed for serious boating. Inside, the home features a fully renovated interior with designer tile flooring, an open-concept layout, and expansive sliding glass doors that seamlessly connect indoor and outdoor living. The chef’s kitchen is equipped with custom cabinetry, a Viking hood system, gas cooktop, and premium appliances, while a temperature-controlled wine cellar adds a true luxury touch. The primary suite is a private retreat with a spacious layout, oversized walk-in closet, and a spa-style bathroom featuring a glass-enclosed shower and outdoor shower access. Every detail has been thoughtfully designed for comfort and functionality. Step outside to your own private resort complete with a saltwater pool and spa, lush landscaping, integrated lighting, and a covered pergola with outdoor lounge space, propane fire pit, and TV viewing area. A retractable awning and outdoor wet bar enhance the space, making it ideal for entertaining year-round. Additional highlights include a 250-gallon propane tank, 14.5 KW generator, updated HVAC, newer water heater with circulating system, epoxy-finished garage, and hurricane protection features. Originally introduced at $2,690,000, the property has undergone multiple strategic price adjustments and is now positioned to sell, presenting one of the best waterfront opportunities on Siesta Key. With nearby properties trading at significant premiums for land value alone, this offering delivers exceptional value for both end-users and investors. Also available: luxury yacht (inquire for details).

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

Listing Agent: Derek Edwards (941-929-3183)