South Sarasota Homes with Two Story Style

South Sarasota Homes with Two Story Style

Welcome to South Sarasota, Florida, a vibrant and picturesque community nestled in the heart of Sarasota County. Known for its stunning natural beauty, South Sarasota offers a perfect blend of coastal charm and suburban comfort. With its lush landscapes, pristine beaches, and a plethora of recreational activities, this area is an idyllic place to call home.

One of the standout features of South Sarasota is its diverse real estate market, particularly the availability of beautiful two-story homes. These spacious residences are designed to cater to modern living, providing ample room for families or those who love to entertain. With elegant architectural styles and thoughtful layouts, two-story homes in South Sarasota often boast expansive living areas, gourmet kitchens, and luxurious master suites. Many of these properties also include outdoor spaces perfect for enjoying the Florida sunshine, whether it’s a private patio, a lush garden, or a sparkling pool.

Living in South Sarasota means you're never far from the area’s rich cultural offerings. Explore the nearby art galleries, indulge in delightful dining experiences, or take advantage of the numerous parks and outdoor spaces that encourage an active lifestyle. Plus, with easy access to the stunning Gulf Coast beaches, residents can enjoy sun-soaked days by the water.

Whether you're seeking a family-friendly neighborhood, a vibrant community, or a serene retreat, South Sarasota has something for everyone. Discover the charm of this delightful city and explore the wonderful two-story homes that await you in this sunny slice of paradise!

Newest South Sarasota Homes with Two Story Style

$680,000
3 Beds 3 Baths A4703532 MLS 1372 BLDG.
Remodeled in 2021 by renowned French interior designer Gaëlle Wizenberg, this 3 bedroom, 2.5 bath townhouse blends European elegance with modern comfort. Thoughtfully upgraded from top to bottom, the home features beautiful oak hardwood floors and porcelain tile throughout, along with newer air conditioning, plumbing, and electrical systems. A series of inviting outdoor spaces enhances the home’s natural charm. Enjoy morning coffee on the front balcony or unwind on the private back terrace, both surrounded by lush vegetation and tranquil, tree-lined views that create a serene retreat. Inside, the gourmet kitchen features Miele appliances including a built-in refrigerator, induction cooktop and convection/microwave steamer oven, creating an elevated culinary environment. Sleek Tesoro quartz countertops complete the space with a refined, contemporary finish. Upstairs, three bedrooms each open to a private balcony, bringing in natural light and fresh air. The shared bathroom features a relaxing soaking tub, while the principal suite offers a walk-in closet and an en-suite bath designed for comfort and privacy. Located within The Landings, one of Sarasota’s most sought-after gated communities, residents enjoy 24-hour security and an impressive array of amenities. The community features a clubhouse, tennis courts, pool, gym, library, and multiple social areas. Convenience is unmatched with shopping, dining, beaches and other recreational venues all within close proximity to this location.

1372 Landings Point Unit 28, South Sarasota

$1,444,900
4 Beds 4 Baths A4702501 MLS
Nestled within the gated community of Portofino on the Bay, an intimate Mediterranean-inspired enclave of just twenty homesites in the Sarasota/Vamo area, this residence offers an inviting coastal setting and an active Florida lifestyle. Enjoy deeded access to Little Sarasota Bay, complete with a community dock, kayak storage and launch, and the potential to purchase a private boat slip with lift separate to community homeowner when available. Double entrance doors open into a two-story foyer, introducing an open-concept floor plan complemented by soft, welcoming wall tones, custom window and door trim, and crown molding across both levels. Plantation windows shutters add a classic touch throughout the entire home—including the garage, which features durable epoxy flooring. In the main living room, an accent stone floor to ceiling gas fireplace serves as a centerpiece for gathering or relaxing in the evening. The adjacent kitchen offers bright, clean-lined soft-close cabinetry, a built-in cooktop, stainless steel appliances, and a convenient closet pantry. The main-floor Owner’s Retreat provides a comfortable private wing, complete with its own dedicated A/C zone (one of three independent systems in the home). The bedroom features a tray ceiling and French doors opening directly to the pool patio. The ensuite bathroom is equipped with dual sinks, a makeup vanity, a walk-in shower, a bidet, a generous walk-in closet with custom built-ins and a tub ready for relaxation with bubbles after a day on the water. A main-floor den with tray ceilings offers flexible space for a home office or reading room, complemented by a main-level guest half bath. Upstairs via the wrought-iron staircase railing, a central loft connects to three additional bedrooms—each accented with tray ceilings. Two of the guest rooms share direct access to a private outdoor balcony, while the fourth bedroom showcases soaring ceiling height and abundant natural light, all cooled by a dedicated second-floor A/C zone. Step out back to the newly extended panoramic-screened lanai, finished with travertine tile surrounding the heated salt-water pool and spa. A convenient pool half bath and an outdoor shower make outdoor living effortless. Situated in an X Flood Zone with no prior hurricane damage, this home is also exceptionally well-located: just a 10-minute drive (6 miles) to world-renowned Siesta Key Beach and 15 minutes (9 miles) to vibrant Downtown Sarasota for premier dining, arts, and shopping. The new Sarasota Square presently being remodel led with approximately 90,000 square feet of daily-needs retail scheduled for delivery in the first quarter of 2027 plus with easy Costco shopping.

1650 Assisi Drive Unit 16, South Sarasota

$11,375,000
4 Beds 8 Baths A4703378 MLS
Some properties offer a view. This extraordinary 1.41 acre Oyster Bay estate offers an entire waterfront world of its own and is one of the best waterfront locations that Sarasota has to offer, with more than 430 feet along Sarasota Bay and a setting that feels virtually irreplaceable. Spanish and Mediterranean inspired architecture lends warmth, character, and timeless sophistication to this remarkable six bedroom residence, while its expansive shoreline creates a front row seat to spectacular sunsets, passing boats, and the natural beauty of Sarasota’s coastal landscape. With access to the Intracoastal Waterway and Gulf of Mexico, this is a rare opportunity for the luxury buyer who believes life is best lived on the water. Spanning more than 10,000 total square feet, with nearly all principal living areas on one level, the home was created for both grand entertaining and relaxed waterfront living. Dramatic ceilings, distinctive architectural details, expansive windows, and a spectacular gallery space with an interior fountain establish a sense of occasion, while multiple intimate gathering areas make the estate equally comfortable for everyday life. A commercial grade chef’s kitchen with professional appliances is equipped for effortless entertaining, from elegant dinners to large celebrations. The primary suite is a private sanctuary framed by beautiful bay views, featuring an expansive custom wardrobe and an indulgent bath with soaking tub, oversized shower, and dedicated massage and sauna room. Five additional bedroom suites provide exceptional privacy for family and guests, each with its own bath and generous storage. Beyond the interiors, the estate unfolds like a private resort. A swimming pool, tennis court, fitness room, billiard room, private office, three car garage, abundant storage, and permitted dock replacement create a property designed for recreation, relaxation, and life on the water. A new roof completed in 2024 adds further value and peace of mind. The address is equally exceptional. Oyster Bay Estates places you near The Field Club, Siesta Key, Southside Village, Sarasota Memorial Hospital, and Downtown Sarasota, offering remarkable access to world class beaches, boating, fine dining, shopping, arts, and culture while remaining tucked within a prestigious waterfront enclave. For those with an even greater vision, the magnificent acreage and extraordinary bay frontage also present the opportunity to create a completely new custom waterfront estate. The property may offer potential for division into two buildable homesites if the existing residence is removed, subject to verification and applicable approvals. With its commanding Sarasota Bay frontage, boating access, acreage, privacy, and coveted location, 1136 N Lake Shore Drive is not simply a place to live. It is the opportunity to claim an extraordinary piece of Sarasota’s waterfront lifestyle.

1136 N Lake Shore Drive, South Sarasota

$225,000
2 Beds 2 Baths A4702878 MLS 5785 BLDG.
Virtually Staged. Welcome to this beautifully updated 2 bedroom, 2 bathroom condo offering a refined blend of comfort, style, and effortless Florida living. Thoughtfully updated throughout, this light-filled residence features LVP flooring throughout the main living areas, inviting indoor and outdoor living spaces, a welcoming front porch, and a private rear porch, along with access to a beautifully maintained community pool. The updated kitchen combines modern style with warm, natural accents, featuring crisp white cabinetry, stainless steel appliances, and custom Acacia wood butcher-block countertops sealed with a water-based polyurethane finish. A sliding glass door off the kitchen opens directly to the private front porch. The spacious primary suite provides a peaceful retreat with a generously sized walk in closet featuring built-in shelving for exceptional storage and organization. The beautifully updated en-suite bathroom continues the home's custom finishes with an Acacia wood butcher-block vanity countertop, also sealed with a water-based polyurethane finish, complemented by a stylish vessel sink and matte-black faucet. A glass-enclosed walk-in shower finished with wood look tile completes this inviting, spa-inspired space. The second bedroom offers excellent flexibility for guests, a home office, or a hobby room and is conveniently served by a full guest bathroom featuring a tub and shower combination with tasteful tile accents. For added everyday convenience, the home includes a full size stacked washer and dryer along with additional shelving, making laundry and storage effortless. Outdoor living is just as inviting, with both a welcoming front porch and private rear porch providing comfortable spaces to enjoy morning coffee, outdoor dining, grilling, or relaxing in the Florida breeze. Residents also enjoy access to a sparkling community pool surrounded by lush landscaping, mature shade trees, and ample lounge seating, creating a peaceful retreat just steps from home. Ideally positioned near Siesta Key, this residence puts some of Sarasota's most desirable beaches, restaurants, shopping, and local attractions within easy reach. Whether you're looking for a full-time residence, seasonal retreat, or low maintenance investment, this beautifully updated condo offers the ideal blend of thoughtful upgrades, private outdoor living, community amenities, and an unbeatable Sarasota location.

5785 Summer Side Lane Unit 4A, South Sarasota

$995,000
3 Beds 2 Baths A4699941 MLS
LIVE THE WATERFRONT & BOATING LIFESTYLE in highly desirable SOUTHPOINTE SHORES! Perfectly positioned DIRECTLY ACROSS THE STREET FROM THE COMMUNITY BOAT RAMP AND DOCK—approximately 100 feet away—this 3BR/2BA home offers exceptional convenience for boating enthusiasts. Keep your boat right on your property, prep it at home, and launch without the hassle or wait of a public boat ramp. At the end of the day, simply back your trailer from your driveway to the ramp, load up, and you're home! Southpointe Shores provides DIRECT ACCESS TO THE INTRACOASTAL WATERWAY and, with the reopening of Midnight Pass, offers convenient access to the Gulf of Mexico—making this an outstanding location for fishing, boating, and enjoying Sarasota's coastal lifestyle. Situated on an 14,000+ SQ. FT. LOT, the property features a large driveway with ample parking for multiple vehicles. A shelled side yard with a substantial privacy gate provides dedicated space for BOAT OR RV PARKING. There's also plenty of room to add a POOL and potentially a large garage, creating even more possibilities for this spacious property. Per the Sarasota County Property Appraiser, the structure is located in ZONE X. A private well at the rear of the property supplies irrigation, while the well house also provides convenient WATER AND POWER for a boat or recreational vehicle. For added peace of mind, the home is PRE-WIRED FOR A GENERATOR CONNECTION capable of powering the entire residence when paired with the appropriate generator. Inside, an open floor plan and large windows create a bright, welcoming living space filled with natural light. The front & rear entry doors, as well as the garage door, are HURRICANE-RATED DOORS, and all windows are protected by HURRICANE SHUTTERS. The spacious kitchen is light and bright with NEWER APPLIANCES, COUNTERTOPS, AND CABINETRY. Both bathrooms have been recently updated, including new in-ground plumbing, tile, and cabinetry. The remodeled primary bath is especially impressive, featuring a LARGE ZERO-ENTRY SHOWER with dual shower heads designed for both standing and seated bathing. The primary suite offers generous space along with a large walk-in closet. With its expansive lot, boat and RV accommodations, numerous updates, and a community boat ramp just steps from the driveway, this Southpointe Shores home offers a rare opportunity to enjoy the Sarasota boating lifestyle with exceptional ease and convenience.

7616 Cove Terrace, South Sarasota

$6,000,000
4 Beds 5 Baths A4701487 MLS
Some homes are built. Others are envisioned. 1516 Ridgewood is the result of an uncompromising pursuit of excellence—a California Pacific Palisades-inspired waterfront estate where timeless architecture, extraordinary craftsmanship, and Sarasota's coveted boating lifestyle converge into one remarkable residence. Completely reimagined with virtually every surface, system, and space thoughtfully transformed, this exceptional home was designed to live as beautifully as it looks. Sunlight pours through expansive impact glass, illuminating sophisticated interiors where clean architectural lines, custom finishes, and seamless indoor-outdoor living create an atmosphere of effortless elegance. Every detail reflects a commitment to quality rarely found in today's market. Anchoring the home is a spectacular chef's kitchen designed for both culinary excellence and unforgettable entertaining. An extraordinary suite of Wolf and Sub-Zero appliances—including an eight-burner gas range with griddle, built-in coffee system, Cove dishwasher, designer refrigeration, oversized pantry, and a dramatic entertaining bar—is complemented by custom cabinetry, multiple beverage centers, ice makers, and a stunning temperature-controlled glass wine room worthy of the finest private collections. The primary suite offers a tranquil retreat inspired by the world's finest luxury resorts, while beautifully redesigned guest suites provide exceptional comfort and privacy. Throughout the residence, Turkish shell stone flooring, TruStile doors, EMTEK hardware, floating custom cabinetry, Level 5 wall finishes, and designer appointments create an understated elegance that feels both warm and sophisticated. Behind the walls lies a level of engineering that is seldom seen. A state-of-the-art Josh AI automation system seamlessly integrates lighting, climate, security, audio, and mechanical systems into one intuitive platform, placing the entire home at your fingertips. Whole-home True Audio speakers, buried fiber connectivity, dedicated IT infrastructure, multiple wireless access points, and integrated security provide technology equal to the home's extraordinary design. Constructed with longevity in mind, the residence showcases impact-rated windows and doors, concrete block construction, spray foam insulation, a standing seam metal roof, elevated mechanical systems, new electrical service, new plumbing, new water and sewer infrastructure, WiFi-enabled tankless water heaters, and countless improvements that reflect an unwavering commitment to enduring quality. Outside, the boundaries between home and resort disappear. A completely reimagined pool, expansive terraces, architectural ceilings, lush tropical landscaping, dramatic landscape lighting, and a fully appointed Wolf outdoor kitchen create an extraordinary backdrop for entertaining beneath Sarasota's spectacular sunsets. For boating enthusiasts, the experience is simply unmatched. With newly dredged water access, newer dock, and no bridges to Sarasota Bay, spontaneous afternoons on the water and unforgettable Gulf sunsets become part of everyday life. More than a luxury residence, 1516 Ridgewood is a home that inspires. It is the rare combination of visionary design, uncompromising construction, intelligent technology, and an incomparable waterfront setting—created for those who believe true luxury is measured not only by beauty, but by the extraordinary way a home makes you feel.

1516 Ridgewood Lane, South Sarasota

$1,925,000
3 Beds 2 Baths A4697757 MLS
ATTENTION BOATERS!! Waterfront dream home – move-in ready! Just a quick (429 yard) boat ride to the ICW - no bridges - a straight shot to the water. Head out to the newly opened Midnight Pass where pristine waters flow freely into the Gulf. 10,000 pound boat lift - gorgeous trex decking - 45+ foot dock with fish stand. Walk to Siesta Key. This beautifully updated waterfront residence offers refined Florida coastal living in a truly exceptional setting. Positioned on a picturesque “Y” intersection of two canals, the property provides serene water views, privacy, and effortless access for deep water boating and outdoor enjoyment—just minutes from Siesta Key’s renowned white sand beaches. A stately approach framed by mature oaks and professional landscaping leads to a custom paver drive and striking hurricane-impact glass entry. Inside, the open, light-filled floor plan showcases original terrazzo and travertine flooring, PGT impact windows, and seamless indoor-outdoor flow. Impact French doors open to expansive gardens, tranquil fountains, a private pool, and classic Chicago brick pavers. Designed for entertaining, the home features multiple outdoor living spaces, including an expansive Trex deck overlooking the canal, a pergola, screened patio, boat dock and covered cabana. The kitchen is appointed with quartz countertops, ceiling-height shaker cabinetry, stainless steel appliances, reverse-osmosis water, and generous windows overlooking the backyard. Living and dining spaces flow effortlessly, complemented by a separate family room, opening to a screened lanai. Renovated guest accommodations complete the main level with 2 bedrooms including sun-drenched guest room, office with Murphy bed and full bath. The second level is devoted entirely to the primary suite, a private retreat with resort quality features as: hardwood floors, water views in every direction, French doors with retractable screens, a private balcony, and a spa-inspired bath with dual vanities, a Carrara-tiled walk-in shower, and custom walk-in closets. Ideally located near Siesta Key, downtown Sarasota, and the region’s cultural, dining, and shopping destinations. Evening relaxation - picture this: you’ve had an amazing day on the water and now you’re ready to cook up your catch right in your own backyard. Perfect sunset dinner awaits! This waterfront gem offers everything you need for the ultimate boaters lifestyle – easy access, premium amenities, and the perfect set up for enjoying your evenings. Ready to make waves in your new home? **No hurricane damage. HOME NOT IN A FLOOD ZONE.

1827 Baywood Drive, South Sarasota

$373,750
2 Beds 2 Baths A4699325 MLS 1646 BLDG.
Live close to Siesta Key Beach, rated in the top ten beaches and in Sarasota, Florida, CNN rated as the #1 city to visit in the United States for under $375,000. This two-bedroom, one and one-half bathroom townhouse unit is just across the south bridge to Siesta Key. A short walk to Crescent Beach, restaurants, shopping, and off-island in season, do not deal with beach traffic. The 1,232 square foot townhouse has two floors, a screened and private covered lanai on the first floor and a private open balcony on the second floor. The living area and the primary upstairs bedroom both overlook a private, tranquil rear yard and greenbelt area for your relaxation and your enjoyment. This townhouse is turn-key furnished, with an inside utility closet with a stack washer/dryer, new extra under stairs, 3 x 6 storage closet and an additional 4 x 6 mechanical closet with the HVAC system, hot water heater and more storage space. This is one of the few units in the complex with inside utility. This unit has been fully renovated by the current owner with all new stainless steel appliances, all new flooring, all new shiplap walling in Dining area, and second-floor full bathroom, with new vanity, and all new stair case and wood risers. Decorated turnkey furnished, this townhouse shows extremely well for one's personal enjoyment and the Siesta Key lifestyle or as an investment property with a one-month minimum rental, three times a year. The monthly condo fee covers the barrel-tile roof which is maintained annually, and the exterior of the building, maintenance and insurance, landscaping, all amenities including on-site management, two heated community pools, one on the intercoastal with water views, a clubhouse, pickleball courts, tennis courts, shuffle board, a mangrove walk, and a gazebo on the intercoastal for fishing or watching sunset. Through the association and paid for with the monthly fees are the financial reserves, basic cable television, water, sewer, trash, recycling, and weekly pest control. Unit #101 assigned and deeded parking space, #163 is on the left of this unit's front door and two guest parking spaces are directly across the driveway from this unit. Other monthly costs are the electric (FPL) $80 a month, and internet (Frontier) $50 a month, on average. Your homeowner's interior insurance is less than $75 a month and the policy is paid through April of 2027. If you want to drive, there is the Gulf Gate Mall a the corner of US41 and Stickney Point Road with shopping, restaurants, hardware, Publix and Detwiler grocery stores. Castel Del Mare has 185 units, borders the intercostal, and owning one of only 16 townhouses is this island community could be yours. The townhouses have no one above them, so more quiet than your normal stack units with another unit above. This townhouse is vacant and easy to see.

1646 Stickney Point Road Unit 101, South Sarasota

$2,997,000
4 Beds 4 Baths A4698598 MLS
Fully renovated waterfront estate in Coral Cove, one of Sarasota’s most desirable West of Trail communities. Set on an elevated 0.59-acre corner lot directly across from the private neighborhood park and boat launch, this British West Indies-style residence offers over 5,012 square feet of updated living space, rare privacy, and the ultimate Sarasota coastal lifestyle. This 4-bedroom, 3.5-bath home has been extensively renovated and thoughtfully redesigned with modern luxury finishes throughout. Major updates include a new metal roof, impact-rated windows and doors, engineered hardwood flooring, solid core interior doors, custom organized closets, two fireplaces, and no flooding during recent hurricanes. The home offers dual primary suites, including a spacious upstairs retreat with a spa-inspired bathroom, freestanding tub, dual vanities, walk-in shower, and oversized custom closet. The chef’s kitchen is the centerpiece of the home, featuring Café Series appliances, Dolomite countertops, soft-close cabinetry, walk-in pantry, waterfall-edge peninsula seating, and a fluted designer range hood. Large living areas, tall ceilings, French doors, and expansive sliders create a bright, open layout designed for seamless indoor-outdoor living. Step outside to a private resort-style backyard with a large pool, limestone pool deck, lush lawn, mature landscaping, new dock, and floating jet ski pad. With the neighborhood boat launch just across the street, this property is ideal for boating, kayaking, paddleboarding, waterfront entertaining, and enjoying the best of Florida living. Located minutes from Siesta Key Beach, Gulf Gate, downtown Sarasota, shopping, dining, marinas, and Sarasota’s arts and culture scene, this Coral Cove waterfront home offers a rare combination of size, elevation, renovation quality, and location.

1707 Caribbean Drive, South Sarasota

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