Homes For Sale in Sarasota 34239 - 231 homes

Remarks: Under contract-accepting backup offers. Welcome to a rare opportunity to own a spacious and beautiful home in the coveted San Remo Estates neighborhood, just before the North Siesta Key Bridge. This 4-bedroom, 3-bath residence offers 2,696 square feet of living space and features a huge bonus room ideal for a media room, home office, gym, or guest suite. The living room's wood-burning fireplace adds warmth and character, while the screened-in pool deck patio and fenced backyard provide the perfect setting for relaxing or entertaining. The home can be customized to your personal preferences. It is currently in the remodel permit process through the City of Sarasota Building Department, offering a unique opportunity for buyers to work directly with our design team. You may select your own cabinetry, flooring, paint colors, lighting, appliances, kitchen island details, hardware, exterior colors, and even choose to add a hot tub spa. While many buyers love the charm of a ranch-style home, this property allows you to transform it into your own vision. Situated on a generous 12,395 sq. ft. lot, the property features beautifully maintained landscaping, a spacious green backyard, and includes a 2-car garage. Whether your dream style is British West Indies, Mid-Century Modern, Cottage, or something entirely custom, the design direction is completely up to you. This is a special opportunity to create a personalized home in one of Sarasota’s most desirable neighborhoods, just minutes from Siesta Key, beaches, dining, and shopping.

Listing is courtesy of: THE STUTZMAN REALTY GROUP, LLC (941-260-0709)

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

Remarks: CASH-FLOW OPPORTUNITY! This INCOME-PRODUCING DUPLEX Two 2bed 1bath units, is already done for you and delivering strong returns with a 7% CAP RATE and SOLID ANNUAL TENANTS IN PLACE. The property has been BEAUTIFULLY UPDATED with all major mechanicals handled, including a NEW ROOF (2021), UPDATED AC UNITS (2021 upstairs and 2018 downstairs), and a FULL RE-PLUMB (2019) with PEX, PVC, and NEW SEWER lines. Both units feature UPDATED KITCHENS AND BATHROOMS along with DURABLE VINYL FLOORING THROUGHOUT, while the upstairs unit includes NEW APPLIANCES, CABINETS, AND COUNTERTOPS. Each unit is INDIVIDUALLY METERED, tenants PAY ALL UTILITIES, and both are currently rented at $1,800 per month to excellent tenants. The downstairs unit is being sold TURNKEY FURNISHED and has previously been used as a SHORT-TERM RENTAL, offering additional income potential. The property is ideally located just 2 miles to downtown Sarasota, Right Next to Arlington park and pool, around the corner from Pinecrest and 3 miles to Bayfront Park, with close proximity to public transportation and the Legacy Trail. Additional highlights include a FULLY FENCED YARD, SHADED BACKYARD SPACE, a LARGE COVERED STORAGE SHED, and PARKING FOR UP TO 5 VEHICLES. NO FLOOD INSURANCE IS REQUIRED with NO FLOODING OR STORM DAMAGE!!! This is a rare opportunity to own an UPDATED, STABLE, CASH-FLOWING PROPERTY from day one.

Listing is courtesy of: FIVE STAR REAL ESTATE OF FLORIDA LLC (904-539-3336)

Listing Agent: Sarah Allbee, Pa (727-285-0843)

Remarks: Under contract-accepting backup offers. Exceptional opportunity in the heart of Sarasota! Located within city limits, this 3-bedroom, 2-bath home offers a rare advantage with legal short-term rental allowance and an established rental history, making it ideal for both investors and primary homeowners. Offered turnkey furnished, this property is truly move-in or rental ready. Immediately walking in you are greeted with the open kitchen, living room, and dining room. Perfect for entertaining and enjoy a catch up of the day at the beach. The thoughtfully designed split floor plan provides privacy for the owner’s suite and guests, while a dedicated office overlooks the expansive backyard. The large, fenced lot creates the perfect setting for entertaining, complete with an open outdoor space and private jacuzzi for relaxing Florida evenings. Positioned in a highly desirable location, this home is walkable to shopping and dining along Siesta Drive, located within the sought-after Southside School District, and just minutes to downtown Sarasota and world-renowned Siesta Key Beach. Whether you’re seeking a full-time residence, vacation home, or income-producing property, this one offers versatility, location, and lifestyle all in one.

Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)

Listing Agent: Kari Klein (941-961-7419)

Remarks: Perfect Investment Property! Discover Your Ideal Retreat at Plaza Gardens in Sarasota! Welcome to this beautifully remodeled, fully furnished two-bedroom condo situated in the heart of Sarasota! Surrounded by lush tropical greenery and well-kept gardens, this boutique-style residence is the perfect escape for those seeking a serene beach getaway. Located just southeast of Siesta Key’s North Bridge, you're only minutes away from stunning Siesta Key beaches for sun-soaked relaxation. Enjoy the convenience of nearby shopping with Morton’s Market and Publix just around the corner. Downtown Sarasota, known for its vibrant shopping, dining, and cultural experiences, is also a short drive away. This thoughtfully designed condo features an open floor plan that maximizes space and comfort. The modern kitchen comes equipped with new stainless steel appliances, stylish cabinetry, and sleek quartz countertops, perfect for meal preparation. With easy-to-maintain wood laminate flooring and a spacious bathroom accessible from both bedrooms, this unit ensures privacy and comfort. The primary suite includes a cozy alcove with a built-in cabinet and chic quartz countertop for a washer and dryer, blending style with functionality. This turn-key condo is an excellent opportunity for seasonal rentals! With low association fees and a prime location, it’s ideal for vacationers looking to experience the charm of Sarasota and its beautiful beaches. Don't miss out on this exceptional chance to own a piece of paradise at Plaza Gardens. Experience the perfect blend of relaxation, convenience, and investment potential today!

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

Listing Agent: Andrea Cohen (786-773-0370)

Remarks: Welcome to your slice of Sarasota paradise! This vibrant, first-floor condo is the ultimate tropical retreat, located just four miles from the world-renowned sands of Siesta Key Beach and a mile from Southside Village. Whether you are searching for a savvy investment, a seasonal vacation getaway, or a low-maintenance primary residence, this home is perfectly positioned for the Florida lifestyle. This move-in ready, west of the trail home, boasts a comprehensive interior renovation that blends modern convenience with natural beauty. The heart of the home is the stunning kitchen, which features brand-new modern white cabinetry, sleek stainless steel appliances, and gorgeous live-edge countertops that provide a unique and organic focal point for your living space. The upgrades continue throughout the entire unit with fresh new flooring, updated fans, and contemporary lighting that create a bright and welcoming atmosphere. The bathroom has been fully refreshed with a new vanity and sinks, ensuring every inch of this home feels crisp and current. Major mechanical updates provide long-term peace of mind, including a water heater installed in 2021 and an air conditioning system from 2017. You will also enjoy the convenience of an indoor laundry room inside the unit. The community recently benefited from a newer roof, providing peace of mind for years to come. Your assigned parking space is situated right in front of your door, making it a breeze to load up your gear for a day at the beach or a trip to the nearby parks. The location is truly unbeatable and keeps you in the heart of everything Sarasota has to offer. You are within walking or biking distance to the Crossings at Siesta Key, where you will find a Publix grocery store, a variety of dining options, and excellent shopping. The neighborhood is also conveniently close to Sarasota Memorial Hospital and a curated selection of upscale local restaurants. With water, sewer, and trash included in the maintenance fee, you can spend less time worrying about bills and more time enjoying the nearby bridge to the coast. Do not miss your chance to own in one of the area's most sought-after hotspots!

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

Listing Agent: Rory Mcdonald (941-961-7247)

Remarks: Under contract-accepting backup offers. Extraordinary Modern Sanctuary on a RARE DOUBLE LOT with Huge Saltwater Infinity-Edge Pool, Breathtaking Resort-Style Backyard Oasis & Brand-New Outdoor Kitchen! Crafted by Majestik Homes—one of Sarasota’s premier luxury builders—this stunning residence delivers innovative design, exceptional craftsmanship, and true resort-caliber living on one of the most desirable double-lot properties available. Boasting 4 bedrooms and 3 bathrooms with soaring 10-foot ceilings, 8-foot doors, and walls of hurricane-rated impact glass, the open-concept layout flows effortlessly from the chef’s kitchen (quartz counters, soft-close cabinetry, Sub-Zero refrigerator, induction cooktop, and premium appliances) into the expansive great room with perfect sightlines to the front and rear yards. The luxurious primary suite opens directly to the patio via sliding glass doors and features dual custom walk-in closets plus a spa-like bath. Three additional bedrooms offer high-end custom closets (two separated by a stylish barn door), while both guest baths are impeccably finished with frameless glass showers and elegant tilework. Premium upgrades include a new 16 SEER AC system, epoxy garage floors with built-in cabinetry, Tesla charging station, natural gas with generator hookup, auto drapes, architectural uplighting, and a private well for irrigation. The true showstopper is the jaw-dropping resort-style backyard on this rare double lot. Your own private Florida oasis awaits: a huge saltwater infinity-edge pool with integrated gas-heated hot tub — fully self-cleaning and self-draining for effortless year-round enjoyment. The expansive Shellock paver deck (cool-to-the-touch, slip-resistant, and ultra-durable) seamlessly connects to a spectacular just-installed (April 2026) custom outdoor kitchen by Paradise Professional Grills. Step into resort-style living with premium Paradise Professional stainless steel appliances—including a powerful built-in multi-burner grill, 3 outdoor refrigerators, and large stainless sink with protective cover. Finished with elegant Avellaero Stone Italian-engineered countertops, the expansive island offers ample prep and serving space, stainless drawers and cabinets, bar seating with footrest, and is perfectly positioned under the covered pergola with ceiling fan and large screen mounted TV. Overlooking the sparkling infinity pool and lush backyard, this entertainer’s dream is ideal for year-round Florida entertaining and al fresco dining. The entire oasis is fully enclosed by premium 6’ white vinyl privacy fencing and framed by mature tropical landscaping and palms for complete seclusion. A dedicated kids’ play area and large chicken coop add family-friendly charm. The second lot is the ultimate game-changer. With its own separate entrance off Hyde Park, this rare extra parcel offers endless possibilities: build a second garage, casita, home gym, pickleball court, expanded outdoor living area, RV/boat storage — whatever your vision demands. No HOA restrictions means total freedom to create your dream compound. Smartly scaled for low-maintenance living yet delivering an enormous, resort-caliber backyard with unmatched privacy and versatility. Just 1 minute to Sarasota Memorial Hospital, 5 minutes to downtown Sarasota, 10 minutes to Siesta Key, and minutes from top schools, beaches, shopping, and I-75. This is a rare opportunity to own a modern luxury home on a double lot!

Listing is courtesy of: RONNIE DEWITT AND ASSOCIATES (941-755-0011)

Listing Agent: Ronnie Dewitt (941-650-2154)

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: 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. 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: Exceptional Harbor Acres modern residence offering 5 bedrooms, including a sunroom converted by the owners into a true 5th bedroom (closet and A/C). Warm contemporary design with seamless indoor-outdoor living. Located in Harbor Acres, one of Sarasota’s most coveted neighborhoods, this exceptional modern residence delivers a rare blend of warm contemporary design, luxury finishes, and seamless indoor-outdoor living. Perfectly scaled for the neighborhood, the open floor plan is flooded with natural light and effortlessly blurs the line between inside and out. The great room features 8-ft pocketing sliders opening to the covered lanai, anchored by a gas fireplace with illuminated floating shelves. The chef’s kitchen is a showpiece with top-of-the-line Miele appliances, solid wood cabinetry, an expansive quartz island, LED lighting, and a butler’s pantry for effortless entertaining. A separate dining room with picturesque windows offers an inviting setting for intimate gatherings, while the adjoining family room provides a relaxed space to unwind. The first-floor primary suite is a serene retreat with walls of windows overlooking lush tropical foliage and a spa-inspired bath featuring a soaking tub and glass shower. A dedicated office/flex room is conveniently located on the main level. Owners thoughtfully converted the sunroom into a 5th bedroom, offering added flexibility for guests or multigenerational living. Sleek open-riser stairs lead upstairs to two en-suite bedrooms providing privacy and comfort.

Listing is courtesy of: MICHAELA DAMM & PARTNERS (941-726-1808)

Listing Agent: Miska Damm (941-726-1808)

Remarks: Investor Alert! Rare opportunity to own a turnkey income-producing property in a prime location! This fully furnished gem features a brand-new pool, all-new impact windows, and a strong rental history with future bookings already in place, cash flow from day one! Don’t miss your chance to add this high-performing asset to your portfolio. Schedule your showing today, opportunities like this don’t last!

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

Listing Agent: Inbal August (917-957-8111)

Remarks: Everything you thought you needed—and knew you wanted—now offered with an unmatched level of value and flexibility. Recently repositioned with an attractive price improvement and now offered turnkey furnished, this exceptional newer construction residence presents a rare opportunity to step into luxury living—or a high-performing rental investment—without delay. Located within the City of Sarasota limits, this home allows for weekly (7-day minimum) rentals, making it uniquely suited for those seeking both personal enjoyment and income potential. The thoughtfully curated furnishings create an immediate, seamless transition for ownership or rental readiness, blending style, comfort, and functionality throughout. Designed to elevate both lifestyle and longevity, the home features a custom ProTee golf simulator, a two-person Equinox infrared sauna, and a Renu Therapy cold plunge, offering a private wellness retreat rarely found in residential properties. Spanning over 5,400 square feet of total living space, the home showcases a clean, contemporary design with expansive glass, natural textures, and effortless indoor-outdoor flow. The resort-style outdoor setting, complete with pool, spa, and dual covered entertaining areas, pairs perfectly with the home’s open interior spaces, state-of-the-art kitchen, and dedicated home theater—creating an environment equally suited for relaxation or hosting. Positioned between Southgate, Arlington Park, and Cherokee Park, and just moments from Southside Village, this residence delivers not only luxury and location, but now an exceptional opportunity to secure a fully realized lifestyle—ready to be enjoyed from day one.

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

Listing Agent: Rudy Dudon (941-234-3991)

Remarks: In the "heart" of the most popular West of Trail neighborhood, step into a rare piece of Sarasota history just a short stroll to Southside Village restaurants and shops, downtown and 2 blocks to Sarasota Memorial Hospital. Behind a classic white picket fence, this 1926 home welcomes you with a generous yard framed by mature landscaping and colorful gardens. A cozy front porch sets the tone for your entrance into timeless architectural details which blend seamlessly with modern updates. Wood floors run throughout the living areas with natural light pouring in through numerous windows. Tall ceilings are complimented by original wood trim. All the details we love in an older home yet with many updates. The main home offers 2,575 sq ft thoughtfully laid out for everyday living and entertaining. The main level features multiple living spaces, separate dining room, a guest bedroom, a dedicated office and laundry room. Upstairs, the spacious owner's suite plus an additional bedroom with ensuite bathroom provide comfort and privacy. The remodeled kitchen is beautifully appointed with granite counters and custom cabinetry AND....a charming 306 sf studio-style guest cottage that has its own entrance and patio. COME SEE THIS BEAUTY, you will LOVE it.

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

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

Remarks: One or more photo(s) has been virtually staged. 3576 San Remo Terrace – A Waterfront Masterpiece in Sarasota Discover the pinnacle of coastal luxury at this exquisite estate, nestled in the highly sought after San Remo Estates. Offering the best views over Roberts Bay, this 6,091-square-foot residence seamlessly blends timeless elegance, modern sophistication, and unparalleled waterfront access. With an unrivaled location & architectural grandeur it is positioned just over the North Bridge to Siesta Key, this estate delivers spectacular bay views without the flood risks or accessibility challenges often associated with barrier island living. Set on the preferred side of San Remo Terrace, the home enjoys mesmerizing sunset panoramas, deep-water access to the Gulf, and a private, tree-lined setting. A grand custom entryway welcomes you into a world of refined luxury, where turquoise water vistas and the gentle movement of passing boats create an immediate sense of tranquility. The circular paver driveway, lush tropical landscaping, and striking architectural design set the tone for an extraordinary living experience. Designed for entertaining and everyday indulgence. The expansive open floor plan is tailored for both grand gatherings and intimate moments. A grand salon, spacious family room, and a fireplace-accented dining space establish an inviting atmosphere for hosting. The chef’s kitchen is a culinary masterpiece, featuring dual islands with exotic stone countertops, a six-burner gas stove with griddle, double ovens, warming drawer, and an oversized refrigerator/freezer—crafted for culinary excellence. A wet bar and 625-bottle climate-controlled wine room provide the ultimate setting for connoisseurs and casual entertainers alike. With 4 bedrooms, 4.5 baths, an oversized office, and a versatile upstairs entertaining space, this home offers unmatched comfort and functionality. The primary suite on the main floor serves as a serene haven, complete with a luxurious en suite bath, while a private guest suite on the second floor ensures exclusivity for visitors. Step outside into a world of unparalleled alfresco luxury. A resort-style infinity-edge pool takes center stage, surrounded by an expansive paver deck with multiple seating and dining areas—perfect for sun-drenched afternoons or moonlit gatherings. Lush landscaping wraps this serene retreat, creating an oasis for relaxation or playful indulgence. For boating enthusiasts, this estate presents unmatched access to Sarasota’s famed waterways. Brand-new dock & 10,000-lb boat lift Kayak & paddleboard access Fortified seawall The Best of Sarasota Living! This home offers effortless proximity to downtown Sarasota, Siesta Key’s award-winning beaches, fine dining, top-tier schools, and world-class healthcare facilities. Don’t miss the rare opportunity to make this timeless, Tuscan, luxurious waterfront estate your own!

Listing is courtesy of: COMPASS FLORIDA LLC (305-851-2820)

Listing Agent: Deanalita Edelson (941-343-7677)

Remarks: West of the Trail location perfect for going to the beach or Downtown. Perfect for a winter getaway or full time living. 2nd floor unit with enclosed patio. Beautiful gardens and trees surround the property. 2 bedroom 1 bath (room for another 1/2 bath), dual sinks, on-site laundry, elevator and pets are welcome! A Washer & Dryer may be installed in the unit.One designated parking spot and guest parking available. Water and basic cable included.

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

Listing Agent: Kelly Anderson (941-320-6115)

Remarks: Price Reduced! Beautifully Updated GOLF COURSE Frontage Home with the ABSOLUTE BEST LOT and BEST Panoramic PRIVATE NATURE GOLF COURSE VIEWS in all of Village Green Club Estates! This Lovely HOME FEATURES: 3 Bedrooms, 2 Baths, 3rd Bedroom makes a perfect Den/Flex Room, Master Suite w/Updated Private Bath w/Granite Counters, Walk-in Closet w/Built-ins plus Slider to Covered Lanai, Open Living Room w/Gorgeous Private Panoramic Golf Course Views, Formal Dining Area, Family Room Area, Updated Kitchen w/Granite Counters and Eating Bar, Stainless Appliances, Pantry Closet; Breakfast Nook w/Slider to Screened Lanai, Updated Hall Bath w/Tub and Granite Counters, HUGE Laundry Room Large Enough to be Used as an Office, House Re-Plumb, Updated w/Windows w/Hurricane Shutters, (2007) Roof, (2022-2023) AC and Hot-Water Heater, Porcelain Tile in all areas except the Master Suite and One Guest Bedroom, Oversized 2 Car Garage, Private Paver Patio Shaded by a Majestic Oak Tree and Designer Landscaping w/Irrigation. COMMUNITY FEATURES: Golf Clubhouse is Close-by. NO CDD Fees plus SUPER Low $100 Annual HOA Fees! This is a Fabulous Location close to Everything - Publix Grocery Store, Walmart, Walgreens, Starbucks, Legacy Bike Trail, Downtown Sarasota Restaurants, I-75, UTC Mall and the Siesta Key Beaches!

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

Listing Agent: Anne Thomas, Pa (941-993-7700)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Live the ultimate Southside Village lifestyle in this one-of-a-kind Craftsman-style home, where charm meets everyday convenience in a rare blend of elegance, craftsmanship, and modern sophistication. Rebuilt to current code in 2014, it offers the refined feel of a coastal farmhouse, with every detail thoughtfully designed for comfort, efficiency, and timeless appeal nestled in one of Sarasota’s most sought-after and walkable neighborhoods. Step through the privacy gates into a lush, fully fenced yard where a rich paver brick driveway, terrace, and walkways guide you through a serene, low-maintenance garden. Featuring artificial turf, vibrant flowering shrubs, and fruit trees, the exterior is not only incredibly private but also immaculately maintained for effortless enjoyment. Every inch of the property has been meticulously manicured, a true testament to the care it has received. Inside, the floor plan strikes the perfect balance between open living and intimate gathering spaces, ideal for both entertaining and everyday living. The kitchen and living room connect seamlessly, creating a warm, functional flow perfect for hosting or simply relaxing at home. The first-floor primary suite is spacious and secluded, featuring his and hers walk-in closets, dual vanities, and a large walk-in shower, a true retreat within the home. Also on the main level is a sun-filled bedroom that offers wonderful flexibility: perfect as a guest room, home office, or children’s playroom. Upstairs in the main house, you'll find an additional bedroom and a generously sized flex space that is ideal for a game room, entertainment room, or home gym, depending on your needs. The detached two-car garage adds both function and charm, offering an upstairs guest suite complete with a full bath, wet bar, and mini-fridge that is greatly suitable for visitors, a private studio, or a quiet home office. This home truly looks like it belongs on the cover of Southern Living or Coastal Living magazine, thanks to its effortless blend of style, warmth, and timeless appeal. Tucked away on one of Sarasota’s most beloved streets, you're just steps from Morton’s Market, Libby’s, and other neighborhood favorites. Located in the highly regarded Southside Elementary School district, the home offers the very best of the West of Trail lifestyle, walkable to restaurants, boutique shops, and Sarasota Memorial Hospital, with easy bike access to downtown Sarasota, St. Armands Circle, and our world-famous beaches. The best of both worlds: a Southside Village residence with a 2014 effective date, blending modern updates with Sarasota’s enduring charm.

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

Listing Agent: Cole Collins (941-350-8360)

Remarks: Craving a low-maintenance, island-inspired lifestyle just moments from sparkling open water, world-famous beaches, and Sarasota’s most coveted destinations? This quaint Florida bungalow located in west of trail delivers the perfect blend of charm, location, and effortless living—just minutes to Siesta Key and steps from the coastal lifestyle you’ve been dreaming of. Tucked away in one of Sarasota’s most desirable “West of the Trail” neighborhoods, 3424 Old Oak Dr has been thoughtfully redesigned to preserve its original character while introducing timeless, modern updates. From the moment you arrive, the lush tropical landscaping, winding garden paths, and private courtyard-style entry create a warm, inviting ambiance that feels like your own hidden oasis. Inside, the home showcases a light-filled, airy design highlighted by vaulted wood-beam ceilings, soft coastal tones, and an open-concept layout that seamlessly blends comfort and style. The beautifully updated kitchen features granite countertops, open shelving, stainless steel appliances, and designer finishes, creating a space that is both functional and visually stunning. The living area centers around a charming wood-burning fireplace, adding warmth and character, while French doors invite natural light and connect indoor and outdoor living spaces effortlessly. The home offers flexible living spaces ideal for a primary residence, seasonal retreat, or income-producing property. Each room reflects a curated, coastal aesthetic with tasteful updates while maintaining the home’s unique bungalow charm. Step outside to your private backyard sanctuary, where a screened-in heated pool is surrounded by mature tropical landscaping, creating a serene and secluded environment perfect for relaxing or entertaining. An outdoor shower adds to the coastal lifestyle experience, while multiple seating areas and garden spaces enhance the home’s tranquil, resort-like feel. Located just minutes from Siesta Key Beach, Southside Village, downtown Sarasota, Sarasota Memorial Hospital, and top-rated dining and shopping, this home offers unmatched convenience paired with a laid-back coastal lifestyle. Rarely does a property combine location, charm, income potential, and lifestyle so seamlessly. This is your opportunity to own a truly special Sarasota bungalow where every day feels like a vacation.

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

Listing Agent: Adnan Dedic (941-726-2917)

Remarks: Auction Property. Fractional Ownership. Live auction 3/312026 12:00 PM - Just down from Pinecraft Park, this quaint ranch home comes available with lots of appeal. The home features 2 bedrooms, full bath, living room, kitchen, and dining area. There is front porch perfect for relaxing and visiting with neighbors as well as an enclosed rear porch with laundry area. Concrete drive and a nice storage building complete the improvements. The home sits on 2 – 40’x40’ Pinecraft lots providing access from Fry or Yoder Ave and the lots are not in the flood plain. Join us for the preview or schedule your own private showing and join us for this exciting auction.

Listing is courtesy of: KAUFMAN REALTY & AUCTIONS (330-231-4211)

Listing Agent: Curtis Yoder (330-204-2447)