Homes for Sale Near Brookside Middle in Sarasota - 642 homes

Remarks: Gulf-front views at the Gulf & Bay Club, resort living on Siesta Key! Ideally on the fifth floor of the A Building in Gulf & Bay Club, this expansive two-bedroom residence showcases sweeping Gulf views and the signature lifestyle only Siesta Key ownership provides. With 1,335 square feet of interior living space and private lanai, this property delivers coastal elegance and remarkable comfort in one of Sarasota’s loved beachfront addresses. An open floor plan with tranquil Gulf/beach views. New luxury vinyl wood flooring through main living space and comfortable carpet in both bedrooms. Designed for effortless entertaining, the open living and dining areas connect seamlessly to a stunning Gulf-facing view, ideal for sunset gatherings or quiet mornings with ocean breezes. The new updated kitchen pairs functionality with style, offering solid wood cabinetry, stone counters, a center island and all new stainless appliances. The primary suite is a private retreat, complete with walk-in closet, lanai access, and a luxurious updated en-suite bath featuring dual vanities and a large shower. The guest suite is a generously sized bedroom which provides privacy for family and visitors. An additional feature is a spacious laundry room. The Gulf & Bay Club on Siesta Key delivers unmatched amenity experience. The building boasts an array of amenities designed to elevate everyday living, including on-site management for added convenience. Two electric vehicle charging stations that are available, three large heated pools with Wi-Fi including one lap pool, 800 feet of private soft white sandy beach, six tennis courts including one Har-Tru court, six pickleball courts, basketball/racquetball/pickleball courts, shuffleboard court, organized seasonal golf for men and women, State-of-the-art fitness center, including free weights and yoga room, six dry saunas, hot tub, two clubhouses, library with books, bar, pool table and TVs. Numerous social activities during season, and the world-famous Siesta Key Beach directly on the beautiful Gulf of Mexico, featuring spectacular sunsets. This property serves as a tranquil retreat in an exceptional location whether you're seeking a permanent residence or a vacation getaway.

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

Listing Agent: Lisa Gullick (941-364-4000)

Remarks: Located less than a mile from the world-famous Siesta Key Beach, this charming 3-bedroom, 2-bathroom home offers the perfect blend of coastal living and everyday convenience. Situated on a spacious lot, the property features a large backyard—ideal for outdoor entertaining, gardening, or simply enjoying Florida’s beautiful weather. A separate shed in the backyard provides additional storage or workspace. Hurricane windows throughout the house as well as an updated AC. Enjoy being just minutes from shopping, restaurants, and entertainment, while still tucked away in a quiet residential setting. Take a relaxing walk or short bike ride to the beach and experience the stunning white quartz sand and breathtaking sunsets that make Siesta Key so special. Whether you’re looking for a primary residence, vacation getaway, or investment opportunity, this home offers endless potential in one of Sarasota’s most desirable locations.

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

Listing Agent: Maryana Zilinskiy (941-744-6065)

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: Enjoy life to the fullest in this 3 bedroom, 3 bath mid-century modern style ranch home, nestled on a near 1/3 acre lot in the sought-after South Gate neighborhood, offering over 2,400 square feet of architecturally updated and meticulously maintained living space. From the moment you arrive, this private sanctuary impresses with iconic palm trees, a custom circular paver driveway, professionally lit landscaping, and a vivid one-of-a-kind patio with a colorful front entry. Inside, the light and bright open-concept floorplan showcases flawless terrazzo flooring and a striking modern contrasted kitchen with stainless steel appliances and a large island with bar-top seating. The kitchen and living areas flow seamlessly into the family and dining room, providing ample gathering space and an entertainment center ready for modern electronics. French doors lead to an almost 40-foot screened lanai overlooking a professionally manicured, fenced, and irrigated backyard accented with coping. The primary bedroom features a private exterior entrance, space for a desk or seating area, and an en-suite bath with a walk-in closet with built-in shelving and safe, a wall-to-wall glass shower with multiple massage jets and bench seating, and a separate water closet. Two additional contemporary bedrooms and bathrooms are located on the opposite side of the home. The remodeled two-car garage is climate controlled and includes a full laundry room with utility sink. Major upgrades and systems include a standing seam metal roof, hurricane-rated impact windows and garage door, tankless water heater, whole-home generator, updated electrical system with new controls, and a plumbing system rerouted with exterior clean-outs for easy access. The home includes both a 100-gallon and 500-gallon propane tank, with the generator operating from the 500-gallon tank and the water heater capable of running from either tank, all serviced on a regular basis. Indoor comfort is enhanced by a professionally maintained HVAC system with in-duct air purification, including UV lighting and a whole-home purification system. Smart-home features allow remote control of the irrigation system, HVAC, alarm system, front door lock, and security cameras. The driveway has been recently resealed, and exterior security lighting surrounds the home. Optional membership to the South Gate Community Association offers social activities and pool access at the historic community center for a nominal fee. Ideally located just minutes to golf courses, boat clubs, Downtown Sarasota dining, shopping, nightlife, cultural events, and the world-famous beaches of Siesta Key.

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

Listing Agent: Alan Macloughlin (941-780-8628)

Remarks: Superb Location. Big Family Retreat. Excellent Investment. Quiet Beach Days. The search for your ultimate beach retreat ends at 436 Canal Road. This 3-bedroom, 3 ½ bath home has all the extras you’re looking for. Your home is located just steps to world famous Siesta Key Beach. You are an easy walk, bike ride, or golf cart drive to Siesta Key Village where you will experience great food, entertainment and eclectic shopping. Enjoy fishing or dropping your kayak or paddleboard off your private community dock to explore Siesta Key by water. Or relax by the west-facing pool shared by only 4 units. At home, use your interior elevator to take you to all four floors. The oversized garage comes with a new garage door, a mini-split AC unit and plenty of room for your golf cart and beach toys. The first floor of living space has an open-plan kitchen with stainless steel appliances, a dining area and living room. There is also a balcony, laundry and half-bath on this floor. The next floor contains 3 spacious bedrooms and 2 baths. The Primary bedroom has an en-suite with dual sinks, both a garden tub and shower, and two walk-in closets. The top level had a surprise flex space that opens to the large roof top terrace with stunning views of the gulf. The flex space currently has 2 twin beds, a wet bar with under-counter sink, and a full bath with shower. Your home has a 2026 Roof, 2-AC units (2025 and 2022), and new Garage Door (2025). The property is currently being utilized as a WEEKLY rental and sleeps 8. The community is pet-friendly (owners only). Seller is grossing $100k using VRBO. Projections of $167,000+ with property manager. Come visit paradise on Siesta Key.

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

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

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: Live in one of Sarasota’s most desirable neighborhoods! This charming home offers two generously sized bedrooms plus a versatile third space that can serve as a sunroom, office, or private in-law suite/studio. This additional area includes its own bathroom, kitchenette, closet, and separate rear entrance—perfect for guests or rental potential. Inside, you’ll find a cozy layout with a welcoming kitchen nook and comfortable living area, ideal for relaxing and unwinding. The home has been thoughtfully updated with a remodeled kitchen, a newer roof (2018), granite vanity top and sink with brushed nickel fixtures (2020), a brand-new water heater (2025), upgraded lighting (2025), and numerous additional improvements throughout. Enjoy your morning coffee on the inviting front porch or entertain and relax on the back patio. The backyard features a two-car carport, storage sheds, and a newly completed, eye-catching stone fence that adds both ambiance and privacy. Conveniently located just minutes from downtown Sarasota, shopping, dining, and the world-famous Siesta Key Beach, as well as other nearby beaches, this home offers both comfort and accessibility. Additional highlights include RV parking and multi-family zoning, providing excellent flexibility and investment potential. Schedule your private showing today and experience everything this beautiful home has to offer!

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: On a lush one-third-acre homesite in desired Pine Bay Estates, this single-story residence has been entirely rebuilt and elevated through a comprehensive, design-forward renovation exceeding $1.1 million. The result is a serene coastal haven where timeless craftsmanship meets modern luxury. A full interior transformation opened the home to light, flow and functionality. The newly relocated chef’s kitchen features bespoke cabinetry, premium finishes and a full suite of Thermador appliances, all thoughtfully positioned to overlook the tropical gardens. Wide-plank flooring carries through every room, complemented by exposed beams, curated lighting and refined architectural details. Every major system has been replaced or upgraded, including all-new HVAC, a tankless water heater, new plumbing and water lines, new insulation, and hurricane-rated windows, doors and sliders, ensuring enduring comfort and peace of mind. The home’s heart is its stunning sunroom, surrounded by glass and bathed in natural light, an ideal space for morning coffee, quiet reading or gathering with guests while taking in the lush, mature landscaping. Three beautifully redesigned baths, a gas fireplace, custom California Closets and a new laundry suite continue the theme of thoughtful luxury throughout. Outside, the home lives like a private botanical retreat. A full landscape redesign brought in layered tropical plantings, ambient lighting, new walkways and hardscape, all-new fencing and gates, and a pool with a replaced deck and rescreened cage. A new roof, fresh stucco exterior, carport enhancements and upgraded exterior lighting, complete the transformation. With its rare combination of single-level living, expansive grounds and meticulous top-to-bottom renovation, this Pine Bay Estates residence offers an inspired West of Trail lifestyle just moments from Southside Village, Siesta Key and Sarasota’s finest dining, beaches and marinas.

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

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

Remarks: 3512 Camino Real represents a rare opportunity to acquire a newly constructed luxury residence strategically positioned for high-performing short-term rental income in one of Sarasota’s most supply-constrained residential corridors. Located inside the City of Sarasota and approximately 10 minutes to Siesta Key Beach, Siesta Key Village, and Downtown Sarasota, this property is purpose-built to operate under a weekly rental model that aligns with current city regulations while attracting higher-quality, longer-stay guests. Unlike many coastal investment properties that rely on nightly rental volatility or regulatory gray areas, this home offers a compliant, predictable income profile paired with strong long-term appreciation fundamentals. Completed in 2025 by award-winning Heritage Builders, the British West Indies–inspired residence spans 3,810 square feet on an oversized .27-acre corner double lot, offering 5 bedrooms, 4.5 bathrooms, a dedicated office, a game room, and a 3-car garage. The layout comfortably sleeps up to 12 guests, supporting premium weekly rates and strong demand across multiple seasons. The home’s interior and exterior amenities are intentionally aligned with today’s luxury short-term rental market: a private heated resort-style pool and spa, expansive covered lanai with outdoor kitchen, open-concept living areas, high ceilings, impact-rated windows, concrete block construction, and elevated hurricane standards. These features enhance guest experience while also reducing operational risk, insurance exposure, and long-term maintenance costs—key considerations for investor underwriting. From an operational standpoint, a weekly rental strategy delivers meaningful advantages: fewer guest turnovers, lower housekeeping and wear-and-tear costs, improved booking stability, and reduced party risk. The surrounding Granada neighborhood further strengthens the investment thesis, offering oak-lined sidewalks, walkable parks, proximity to boating access, Southside Village dining, and Downtown Sarasota’s cultural and marina district—all while remaining above the flood zone, a critical differentiator for long-term ownership and asset resilience. Beyond income potential, 3512 Camino Real offers multiple exit strategies. Its new-construction pedigree, desirable residential setting, and luxury finish level support future resale to primary residents, second-home buyers, or continued investor ownership. Limited supply of large, newly built homes with pools inside Sarasota city limits underpins long-term value appreciation and broad buyer appeal across market cycles. A comprehensive Short-Term Rental Investor Report, including projected revenue, operating assumptions, conservative and upside scenarios, and long-term investment analysis, is available upon request and is attached in the MLS for qualified buyers.

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

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

Remarks: LOCATION, LOCATION, LOCATION! Imagine pulling into a peaceful cul-de-sac in the ultra-desirable **West of Trail** neighborhood—right between Granada and Oyster Bay—and stepping into your own slice of coastal paradise. This **stunning 4-bedroom, 3-bath pool home** blends custom contemporary coastal style with timeless traditional charm, and it's ready for you to move right in. Best of all? You sidestep the notorious island traffic headaches while staying close enough to zip to everything Sarasota offers quickly. Nestled in the **county** (not city limits) and safely **outside any flood zone**, this home delivers an open floor plan that's perfectly balanced—not overwhelmingly vast, but thoughtfully designed for effortless everyday living and effortless entertaining. Flooded with natural light, the interior glows in warm neutrals and high-end finishes that feel sophisticated yet welcoming. The **show-stopping chef’s kitchen** is truly the heart of the home: sleek new luxury appliances, custom cabinetry, and elegant quartz countertops that make cooking a joy—whether you're whipping up weeknight dinners or hosting friends. Downstairs, a dedicated office offers the ideal work-from-home setup. Upstairs, a versatile bonus loft awaits as your second living room, play area, media room, or whatever your lifestyle needs. The spacious ground floor primary suite and additional bedrooms are generously sized and beautifully appointed, served by three stylish bathrooms. Step outside and you'll find your private **poolside oasis**—complete with a **saltwater pool and spa**, built-in BBQ grill with sink, and lush, mature landscaping with evening lighting. The fully fenced yard is pet-friendly, serene, and perfect for Florida evenings under the stars. Recent upgrades make this home move-in ready and worry-free: - Standing seam aluminum metal roof replaced 2023 - Spacious 3-car garage with durable, easy-clean polyaspartic flaked flooring + extra laundry hookups - Huge attic storage above the garage. - Effective build year 2020 per county records - New hot water heater - Whole-house water softening/filtration system + RO drinking water in the kitchen And the location? Unbeatable. You're in a **walkable, golf-cart-friendly** neighborhood just minutes from everything that makes Sarasota special: - 10 minutes to vibrant **Downtown Sarasota** and world-famous **Siesta Key Beach** - Walking distance to Publix, Red Rock Park, and local eateries - Quick drive to Trader Joe’s, Cinebistro, and the Siesta Key Bridge (great for fishing!) This is more than a house—it's a lifestyle upgrade wrapped in luxury, function, and prime Sarasota convenience. Don't miss your chance to call this beauty home. Schedule your private showing today—your dream coastal retreat is waiting!

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

Listing Agent: Brandon Surline, Pll (941-404-9334)

Remarks: Welcome to ‘The Retreat at Tidewood’, a boater’s paradise nestled in one of Sarasota’s most desirable and secluded waterfront communities. Imagine living just minutes from downtown, fine dining, and shopping, all without the hassle of an HOA. This home offers the perfect blend of convenience and tranquility for those who love life on the water. Elevated 12 feet, this residence ensures peace of mind protection from flooding. Step inside to discover an updated gourmet kitchen with custom cabinetry and premium finishes, a spacious living and dining room, and a luxurious master suite with Venetian Plastering and his-and-hers closets. Every room on the ground floor opens directly to the pool, creating a seamless indoor-outdoor flow to over 2,500 sq. ft. of screened outdoor living — perfect for entertaining or relaxing in total privacy. For the avid boater, the property features a concrete seawall for easy canoe or kayak launching, making it effortless to explore the serene Intercoastal Waterway. Additionally, a boat yard just a short distance away accommodates larger watercraft and offers concierge services, ensuring your boating adventures are always within reach. Upstairs, a private “in-law suite” is accessible by elevator or stairs and includes three flexible rooms, full bath with tub/shower combo, kitchenette, a large walk-in closet, room to add an additional bathroom, and a screened porch overlooking the tranquil waterway, Siesta Key, and timeless sunsets. Surrounded by protected mangroves, the views are as peaceful as they are timeless. Designed for multi-generational living or hosting guests with ease, this home blends thoughtful functionality with waterfront luxury. Its location combines seclusion and convenience — tucked away in a peaceful community, yet close to everything Sarasota has to offer. The adjacent lot could also be purchased for additional acreage, offering even more space and potential. The ‘Retreat at Tidewood’ offers a once-in-a-lifetime opportunity to own a piece of paradise. This unique experience awaits you with the perfect blend of comfort, privacy, coastal beauty, and a lifestyle tailored for those who cherish the water.

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

Listing Agent: Nancy Grenier (941-364-4000)

Remarks: Welcome to this elegant 2017 constructed 'better than new' home that combines the convenience of easy access to Sarasota’s best parks, markets, restaurants, and top-rated schools, with a quiet, friendly neighborhood— plus just a short drive to world-famous sugar-sand beaches of Siesta Key and Lido Beach. Nestled on a lush corner lot in the heart of highly sought-after Arlington Park, this 3-bedroom, 2.5-bathroom residence offers 1,969 heated Sq Ft of beautifully finished craftsman style living and a spacious 2-car garage. The home has been meticulously maintained and thoughtfully upgraded to satisfy the comfort and conveniences required by today's modern lifestyle. You’ll be immediately impressed by the pristine curb appeal and the drama of the grand foyer showcasing soaring 20+ foot ceilings, adding to the home's modern style and open feel. Thoughtful details abound, including crown molding, gorgeous hardwood floors, and exquisite finishes throughout, accented by an abundance of natural light. The formal living and dining rooms create an ideal space for entertaining, while the well-appointed chef’s kitchen is a true showstopper—complete with quartz countertops, custom solid wood cabinetry, stainless steel appliances, a large island, pendant and recessed lighting, and a beautiful backsplash. The kitchen overlooks the bright and inviting combined family and dining area, seamlessly connecting the heart of the home. Upstairs, the huge master suite offers a peaceful retreat, featuring plush carpeting, a spacious walk-in closet, and a luxurious en-suite bathroom with dual vanities and a stunning dual-head walk-in shower. Two additional light-filled bedrooms provide plenty of space for family or guests. Outside is your expansive covered brick-paved patio, perfect for quiet evenings or entertainment, all within a fully fenced backyard with ample room to add a pool. Lush landscaping has been strategically positioned to provide the home with privacy while maintaining a sleek contemporary theme. Additional upgrades include a new A/C unit, new gutters, new washer & dryer, an alarm system, insulated garage door, EV charger, and a new refrigerator. This move-in ready charmer is truly better than new, and offers it all — style, space, and a prime Sarasota location!

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)

Listing Agent: Kathy Callahan (941-900-8088)

Remarks: The Windemere II is an extraordinary luxury custom home meticulously crafted by Heritage Builders. This coastal contemporary residence with clean lines is situated on a very rare West-of-Trail lakefront estate home site. The exquisite two-level residence redefines custom home living, flawlessly blending elegance, sophistication and comfort. As you step in the grand foyer, you are greeted by an expansive, open concept living space that seamlessly integrates the living, dining and kitchen areas. The gourmet kitchen is a chef’s dream, featuring top-of-the-line appliances, custom cabinetry and vast walk-in working pantry. This stunning home boasts four bedrooms, five luxurious baths and two convenient half baths. The primary suite, located on the first level overlooks the sparkling lake and features a designer bathroom private outdoor shower. For those who love to entertain, the Windemere II does not disappoint. Enjoy movie nights in the dedicated media room or host family gatherings in the versatile bonus room. A private study provides tranquil workspace. Ascend via the elegant custom staircase or convenient elevator to the upper level, where you will find two additional en-suite bedrooms, a large bonus room with wet bar and fitness room. Enjoy leisurely moments on the balcony overlooking the serene lake. Step through the massive pocketing sliding glass doors to discover your personal lakefront oasis – a breathtaking outdoor living retreat with a custom pool and spa and a fully equipped outdoor kitchen. Gather around the fire pit, perfect for cozy evenings under the stars. The Windemere II is not just a custom residence; it is a lifestyle. Experience the epitome of high-end-living and schedule a tour today! Floor plan located in attachments.

Listing is courtesy of: HB REALTY GROUP INC. (941-378-3983)

Listing Agent: Sara Boudarga (941-321-6352)

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)

Remarks: The Boatyard is a New England styled gated community of twenty one units located on the Intracoastal Waterway just across the south bridge from Siesta Key and its number one rated beach. Nearby are numerous opportunities for the shopping, dining, sports, and cultural activites that Sarasota is famous for. This furnished two bedroom, two bath unit feaures water views from most rooms, a bright open concept living/dining room with a tray ceiling, a wood burning fireplace, an enclosed balcony overlooking the water, updated kitchen and bathrooms, an oversized one car garage, a bonus room on the canal, and a 27 foot boat slip.In addition, the community amenities include a sundeck on the bay, a boardwalk along the canal, and a heated swimming pool. This is the Florida lifestyle you've been looking for.

Listing is courtesy of: ALAN J STEVENS (941-925-1818)

Listing Agent: Murphy Stevens (941-925-1818)

Remarks: The Boatyard is a New England styled gated community of twenty one units located on the Intracoastal Waterway just across the south bridge from Siesta Key and its number one rated beach. Nearby are numerous opportunities for the shopping, dining, sports, and cultural activies that Sarasota is famous for. This furnished two bedroom, two bath unit features water views from most rooms, a bright open concept living/dining room with a tray ceiling and wood burning fireplace, an enclosed balcony overlooking a canal, updated kitchen and bathrooms, an oversized one car garage, and a ground level bonus room off the canal. In addition, the community amenities include a sundeck on the intracoastal waterway, a boardwalk along the canal, and a heated swimming pool. This is the Florida lifestyle you've been looking for.

Listing is courtesy of: ALAN J STEVENS (941-925-1818)

Listing Agent: Murphy Stevens (941-925-1818)

Remarks: Located West of Trail, this beautiful new construction five-bedroom, five-and-a-half-bathroom residence captures the essence of Sarasota living. Designed with both comfort and entertaining in mind, the home features expansive sliding glass doors that open the main living areas to a private pool and outdoor gathering space, creating a seamless connection between indoor and outdoor living. Inside, generous living spaces, clean architectural lines, and refined finishes create a warm yet modern atmosphere. The open-concept layout centers around a spacious kitchen and living area, ideal for everyday living while also providing an elegant setting for hosting family and friends. Upstairs, well-appointed bedroom suites give privacy and flexibility, while the primary suite provides a peaceful retreat with a spa-like bath and thoughtfully designed closet space. Every detail of the home has been carefully considered to deliver both functionality and timeless style. Thoughtfully designed for comfort and ease, the property offers a low-maintenance lifestyle that appeals to both full-time residents and seasonal owners looking for a lock-and-leave Sarasota home. Ideally located just minutes from Southside Village, downtown Sarasota, Sarasota Memorial Hospital, and the Gulf beaches, the home places you close to the best dining, shopping, and coastal experiences the area has to offer while maintaining the quiet charm that has long made West of Trail one of Sarasota’s most desirable neighborhoods.

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

Listing Agent: Steven Moore (401-767-7180)

Remarks: You found it! A home that blends comfort, functionality, and Florida-style outdoor living—all with the freedom of NO HOA! This beautifully maintained single-family residence invites you in with a charming curb appeal featuring coach lights, gutters, and a decorative tile entryway that sets the tone from the moment you arrive. Enjoy the convenience of keyless entry and a thoughtfully designed garage with a side door to the exterior, perfect for easy access and added flexibility. Inside you’ll find a spacious, light-filled layout where everyday living and entertaining come together effortlessly. The living room is anchored by a custom media center, creating the perfect space for relaxing nights or hosting guests. The kitchen is both practical and inviting, offering an eat-in area, a separate dining space, and a unique pass-through serving window to the patio—ideal for seamless indoor-outdoor entertaining. Slide open multiple glass doors and step out to your private backyard oasis overlooking a tranquil pond view. Whether you’re enjoying your morning coffee, hosting a barbecue on the extended concrete slab, or soaking up the Florida sunshine, this outdoor space is designed to impress. Inside you’ll also find spacious guest bedrooms, each offering comfort and versatility, along with multiple double-door closets throughout the home—providing an abundance of storage options. Ceiling fans enhance comfort year-round, while hurricane shutters add peace of mind during storm season. This home truly checks all the boxes: VALUE, space, and smart features—all in a serene setting with no HOA restrictions. Seller offering a home warranty with approved offer …or add some updates to your own preference!

Listing is courtesy of: KEY TO FLORIDA REALTY (239-776-9260)

Listing Agent: Rhonda Ryals (813-368-6759)

Remarks: LAKEFRONT VALUE with Stunning Views in this Luxury End Unit, that is "Low-Cost Living" in sought after Lake Arrowhead. This end unit condo offers 3 Bedrooms and 3 Bathrooms and is completely remodeled! The air conditioner and heat pump were replaced in April 2026 and the updated chef's kitchen is high-end quality with custom cabinetry, stainless appliances and quartz tops. $539/month in low HOA fees covers the roofs and includes much of your insurance cost! Rarely available, this 1,800 square foot condo offers comfortable living with high-end finishes throughout. The enclosed 3rd bedroom offers a large walk-in closet and private bathroom and it currently is used as an entertaining lounge area with incredible views of the lake and wildlife through the floor to ceiling windows! Furniture is negotiable! HOA fees include cable, pest control, exterior maintenance and lawn care. At this price, this condo is more affordable than most residential homes! Lake Arrowhead is a hidden gem in South Sarasota with lush landscaping and lakes. The Great Room with high ceilings has a large sliding glass door that opens onto the spacious, covered lanai that overlooks the lake with a very peaceful view. The Key West Clubhouses is next door and is steps away for convenience. Enjoy the heated community pool, the large community room-kitchen-library in the clubhouse and the fishing pier. This is value priced for a larger condo in Lake Arrowhead and this condo is one-of-a-kind with it's fine finishes! Management is on-site and this condo includes one carport space. This community has everything you could desire and is located next to the 72-acre Red Bug Slough Preserve that is pet friendly and has several miles of hiking trails, a playground, picnic shelters & a fishing dock. Lake Arrowhead consists of 64 condos which is conveniently located to everything, including the World Renowned Siesta Key Beaches, Legacy Trail, Costco, several fitness centers, Publix, A+ Schools, Fine Restaurants and the Gulf Gate Library. UTC Mall and cultural downtown Sarasota are within 20 minutes for opera, movie theaters, dining, Selby Gardens & more! Make this your favorite place to relax and unwind as you are surrounded by tropical landscaping and lake views from nearly every room. Come and see this amazing condo; EZ show!

Listing is courtesy of: DEBBIE HERING REALTY & ASSOC. (941-320-1070)

Listing Agent: Debbie Hering (941-320-1070)