286 houses for sale in Southside Village

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Under Construction. All photos of the interior and exterior attached are only representative examples of possible fit and finish selections from the builder. Welcome to a rare opportunity to secure a striking, under-construction contemporary estate in the coveted Arlington Park neighborhood of Sarasota. Scheduled for completion by the 3rd qtr of 2026, this architecturally distinctive luxury residence is designed for the most discerning new-construction buyer who values elevated design, cutting-edge finishes, and seamless indoor-outdoor living. Spanning 3,117 square feet, this 4-bedroom, 4.5 bath custom home showcases a light-filled open floor plan curated for modern elegance and effortless entertaining. Expansive porcelain tile flooring flows throughout, enhancing the clean, contemporary aesthetic. At the heart of the home, a show-stopping chefs kitchen features a premium appliance package, quartz countertops, a dramatic waterfall-edge island, oversized walk-in pantry, and whole-house

Rarely available 2001 built one story home on a 75 ft wide lot in the prime heart of West of Trailu002F Southside Village area. One block to Sarasota Memorial Hospital and 3 blocks to the ever popular Southside Village shops and restaurants. A 'true' neighborhood, Hudson Bayou is one of the most sought after areas to live in. This 4 bedroom (split bedroom plan) 3 full bath pool home has high ceilings and an oversized 2 car garage. The primary bathroom has a curbless oversized shower

Virtually Staged. West of Trail luxury meets modern innovation at 1759 Waldemere Street. This brand-new, custom-built residence embodies timeless design, contemporary craftsmanship, and intentional indoor–outdoor living. Set on a. 33-acre lot just steps from Southside Village and Sarasota Memorial, the home delivers sophistication, convenience, and exceptional attention to detail in one of Sarasota’s most sought-after neighborhoods — a rare opportunity in the coveted West of Trail community. Spanning 4,513 square feet, the two-story floor plan features four bedrooms, five baths, an office with private entry, and a media room that opens to a 480-square-foot balcony overlooking the property. Designed for both everyday living and elegant entertaining, the home showcases expansive sliding glass doors that blur the line between indoors and out, opening to a heated saltwater pool, spa, and lush landscaped backyard for year-round enjoyment. The designer kitchen serves as the heart of the home

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

Sandy Hook stands as a rare fusion of history, architecture, and coastal living. Sandy Hook is Siesta Keys Premier Gulfside Community. Just north and west of Siesta Village, Sandy Hook is more than a neighborhoodits a legacy. Widely regarded as one of the most prestigious, desirable, and coveted communities on Siesta Key, it sits on a stretch of coastline where Gulf breezes carry stories of visionaries and architects who defined modern Florida living. Sandy Hook, with its private entrance, features a private beach, the epitome of the ultimate island lifestyle. This oversized Southern Exposure Lot of 38, 435 square feet lagoon-front lot offers endless possibilitiesreimagine and remodel the existing home or tear down and build your dream island retreat with Gulf and beach views. With direct frontage on the lagoon, you can design your own dock or kayak launch for seamless access to the water. Though the home was impacted during the storm, the opportunity here is extraordinary: remodel wha

Sandy Hook stands as a rare fusion of history, architecture, and coastal living. Sandy Hook is Siesta Keys Premier Gulfside Community. Just north and west of Siesta Village, Sandy Hook is more than a neighborhoodits a legacy. Widely regarded as one of the most prestigious, desirable, and coveted communities on Siesta Key, it sits on a stretch of coastline where Gulf breezes carry stories of visionaries and architects who defined modern Florida living. Sandy Hook, with its private entrance, features a private beach, the epitome of the ultimate island lifestyle. This oversized Southern Exposure Lot of 38, 435 square feet lagoon-front lot offers endless possibilitiesreimagine and remodel the existing home or tear down and build your dream island retreat with Gulf and beach views. With direct frontage on the lagoon, you can design your own dock or kayak launch for seamless access to the water. Though the home was impacted during the storm, the opportunity here is extraordinary: remodel wha

Condo at 290 Cocoanut Ave #803, Sarasota, FLReference: 36113 A4655045Key Features Ref: 36113-A4655045

Single Family Home at 1774 Cherokee Dr, Sarasota, FLReference: 36113 A4669184Key Features Ref: 36113-A4669184

Condo at 290 Cocoanut Ave #803, Sarasota, FLReference: 36113 A4655045Key Features Ref: 36113-A4655045

Single Family Home at 1774 Cherokee Dr, Sarasota, FLReference: 36113 A4669184Key Features Ref: 36113-A4669184

Condo at 290 Cocoanut Ave #803, Sarasota, FLReference: 36113 A4655045Key Features Ref: 36113-A4655045

Single Family Home at 1774 Cherokee Dr, Sarasota, FLReference: 36113 A4669184Key Features Ref: 36113-A4669184

Dreaming of breathtaking sunsets? This property is for you! A one of a kind bayfront lot located in highly sought-after Cherokee Park, West of Trail. Located in'X' flood zone this property offers unobstructed panoramic views of Sarasota Bay. The stunning vistas of Ringling Bridge, Siesta Key and downtown are truly mesmerizing. Boating enthusiasts will appreciate the brand-new dock with a 16,000lb lift and direct access to Sarasota's exceptional boating waters. Enjoy the home as it is or take advantage of this rare opportunity to build a custom waterfront estate on this magnificent property. Offered at $6,990,000, do not miss your chance to own one of Sarasota's finest waterfront locations

Stunning New Construction by Award-Winning Architect Dan Lear in coveted West of Trail Neighborhood This meticulously designed luxury home offers the perfect blend of modern elegance and timeless sophistication. Near Selby Gardens, Morton's Market, and Sarasota Memorial Hospital, this exceptional property provides both convenience and style. Spanning over 3,800sqft of living area, this expansive residence boasts four spacious bedrooms, five full bathrooms, a enormous den with terrace, and a dedicated office space, all thoughtfully crafted for contemporary living. The grand, open-concept great room is the heart of the home, seamlessly floating over the pool area with a stunning large corner pocketing glass door that connects the interior to the beautifully landscaped outdoor oasis. The second floor features three guest suites, each with its own private terrace, offering tropical views and tranquility. The home's striking exterior showcases luxurious vein-cut travertine, creating a refin

Between North Siesta Key and Oyster Bay, this coastal craftsman contemporary residence offers the leisure of a maintenance-free lifestyle in a desirable location. Visit nearby shopping and dining, or just a quick drive to Siesta Key Beach or downtown Sarasota. Positioned across from the community pool, the home offers easy-care landscaping complemented by a charming herb garden. Built of solid concrete block construction for lasting durability, recent improvements include new UV purification in air-conditioning units, a new roof and fresh exterior paint. The well-designed floor plan offers four bedrooms and three baths, with a flowing open layout that connects the great room, dining area and kitchen beneath high ceilings filled with natural light. A private guest suite above the garage provides flexible space for multi-generational living, a studio or fitness retreat. Throughout the home, refined details like solid-wood cabinetry, deep-trimmed windows and fine millwork reflect craftsma

An Exquisite Bayfront Residence on Prestigious Lido Key, Sarasota. This meticulously reimagined two-story bayfront masterpiece embodies the pinnacle of sophisticated coastal living. Offering 3,832 square feet of thoughtfully designed interior space which was fully renovated in 2017, including impact-resistant doors and windows and a new roof. The residence features 4 ensuite bedrooms, a state-of-the-art 2025 gourmet kitchen, designed for discerning entertainers, showcases premium appliances, custom cabinetry, and an expansive island that serves as the heart of the open-plan living areas. The new elegant flooring unifies the bright, voluminous interiors. The second story includes a spacious home office with views over the pool to the bay. Beyond the interiors lies a private waterfront sanctuary: a heated saltwater pool overlooks an expansive floating dock, ideally suited for vessels of varying sizes, kayaks, or paddleboards. Unobstructed sailboat access invites effortless exploration of