Properties For Sale in Southwood Street, Siesta Key

Immaculately maintained 3-bedroom, 2-bath home near Siesta Key beaches. Features include a wood-burning fireplace, hurricane panels, a screened patio, and a private garden. Conveniently located near parks, shopping, and more. No HOA fees!

Beautifully renovated 2-bedroom, 2-bathroom pool home in Sarasota, Florida. Features updated kitchen, spacious 0.28-acre lot with private heated saltwater pool, screened lanai, and fenced backyard bordering Phillippi Estate Park. Close to Siesta Key Beach and amenities.

Prime 1.3 acre corner lot in West of the Trail, Sarasota. Build your dream home near Siesta Key Beach, upscale shopping, dining, and Phillippi Estate Park. Ideal for discerning builders or those with a vision for an extraordinary legacy.

1.41-acre waterfront estate on Sarasota Bay with 430ft of bay frontage. 6 bedrooms, 6 baths, 10,226 sq ft. Features include a commercial-grade kitchen, tennis court, pool, and more. Ideal for large gatherings or redevelopment.

Waterfront property on Siesta Key needs updating but offers great value. Features include a seawall with dock, deep boating water, two primary suites, pool, and a quiet cul-de-sac location. Close to the ICW, beach, and village.

Luxury waterfront home in Siesta Key with 4 bedrooms, 4.5 baths, pool, and stunning waterfront views. Open concept living, private balconies, and VIP suite. Perfect for those seeking upscale coastal living.

Luxury waterfront home on Siesta Key with 4 bedrooms, 3.5 baths, pool, dock, and amazing views. Perfect for full-time living or vacation retreat. Close to Siesta Beach and Siesta Village.

Luxury waterfront property on Siesta Key with 4 bedrooms, 5 bathrooms, a media room, and 2 separate living areas. Enjoy an open floor plan, expansive lanai, saltwater pool & spa, and new seawall. Estimated completion April 2025.

Luxury waterfront property on Siesta Key, boasting a Florida Modern Design. Features 4 spacious bedrooms, 4.5 baths, open floor plan, private guest suite, saltwater pool & spa, covered lanai, and roof terrace with waterfront views. New seawall, dock & boat lift. Estimated completion June 2025.

Brand new 3,035 sq ft home in Oyster Bay Estates. Features open living spaces, contemporary architecture, island kitchen, primary suite with luxurious bath, 2 en suite bedrooms, study, covered lanai, bonus room with bath, 3-car garage, heated pool/spa, and more.

Siesta Key dream compound! Two updated residences, lagoon-style pool, steps from the beach. Perfect family home or lucrative rental investment. New roofs, storm-impact windows.

Luxurious Siesta Key home with 7-car garage, stunning bay views, private pool & spa, elevator, and Generac generator. Open-concept living, gourmet kitchen, and expansive outdoor entertaining areas. Near Siesta Key Beach.

Newly renovated 3-bedroom, 2-bath home on Siesta Key, steps from the beach! Features a saltwater pool, updated kitchen with stainless steel appliances, and a 2-car garage. Perfect for beach lovers seeking modern comfort.

Fully furnished 2006 Eslinger home on Siesta Key with a new metal roof, open floor plan, updated kitchen, private pool, and over 1000 sq ft of garage space. Perfect for those seeking a luxurious island lifestyle.

Rare opportunity! Charming private home on almost an acre, directly on Big Pass with incredible views. 3,844 sq ft, 4 bedrooms, 4.5 bathrooms, open concept living space, private beach access. Perfect for multi-generational families seeking waterfront living with privacy and easy access to Siesta Key's amenities and Sarasota.

Rare 1-acre waterfront lot on Siesta Key with private dock, offering easy access to beaches, boating, and Sarasota's vibrant city life. Ideal for those seeking a luxurious, secluded island retreat.

Rare opportunity! This stunning 4 bed/3 bath home in a gated community is one block from Siesta Key Beach. Features an open floor plan, pool, lanai, outdoor kitchen, and impact windows. Fully furnished!

Luxury waterfront home on Siesta Key's Grand Canal. 4 spacious en-suite bedrooms, gourmet kitchen, pool, spa, boat lifts, & stunning canal views. Minutes to Siesta Beach & Village. Optional 675 sq ft bonus room.

New build 5 bed, 5.5 bath home in Siesta Key, a few minutes from the beach. Features include an elevator, chef's kitchen, outdoor kitchen, open floor plan, modern finishes, pool, and hot tub. Boat dock access to Sarasota Bay.

Build your dream home on this expansive 13,345 sq ft lot in Siesta Key's north end. Enjoy 97 feet of lake frontage, plus quick access to beaches, downtown Sarasota, and Siesta Key Village. Perfect for families seeking serene coastal living with convenient amenities.

Coastal waterfront dream home on Siesta Key. 4 bedrooms, 4 baths, 5,988 sq ft. Updated kitchen with Wolf appliances, pool, dock, boat lift. Hurricane unscathed.

Waterfront lot on Siesta Key's Hansen Bayou, perfect for building a dream home. Features a dock and boat lift, offering easy access to boating and nature. Close to the North Bridge for convenient mainland access. Ideal for those seeking luxury and tranquility.

Beautifully designed waterfront home on a large lot near Siesta Key Beach. Features 5 bedrooms, a 3-car garage, a pool, and an in-law suite. Hurricane-rated windows and sliding doors offer protection. Enjoy serene water views and easy access to shops and restaurants.

Sophisticated 3-bedroom, 3-bath Siesta Key home on the Grand Canal, renovated in 2021. Features a pristine pool, modern kitchen, hurricane impact windows, and a reinforced composite dock with a boat lift. Ideal for boating enthusiasts.

Gulf-front lot, 52,121 sq ft, 141 ft of frontage. Build your dream home with unobstructed views and private beach access. Ready for construction. Rare opportunity!

Luxurious contemporary beachfront home with private rooftop pool, expansive owners' suite, and stunning Gulf views. Flexible layout offers conversion possibilities. A true architectural masterpiece.

Wonderful Siesta Key home, short walk to the beach! 3 bedrooms, 3 bathrooms, theater room, boat dock, elevator, and fully furnished. Perfect for families and boating enthusiasts.

Luxury waterfront estate West of the Trail with direct bay access, 4 bedrooms, 4 baths, private cabana, chef's kitchen, resort-style pool, and fully renovated dock. Perfect for those seeking upscale, convenient bayfront living.

Three-bedroom, two-bath pool home on Siesta Key, recently painted, new roof (2014), re-plumbed (2011). Spacious yard, private pool, and garage. Perfect for a vacation home or permanent residence, offering easy access to the beach and village.

Magnificent Neo-Classical Italian Renaissance Villa on 1.21 Bayfront acres. Panoramic water views, 10,697 sq ft plus 4,185 sq ft garages/storage. 4 bedrooms, 4 baths. High-end finishes, Italian design details, expansive outdoor spaces including pool, outdoor kitchen, and dock with boat lift. A truly unique and luxurious estate.

Mediterranean-style estate on Siesta Key, minutes from the beach. Features 4 bedrooms, a private master suite, open-concept living area, pool, spa, and fully furnished. Perfect for entertaining and relaxed coastal living. New roof in 2025.

Serene West of the Trail oasis! This 3-bed, 3-bath home boasts a spacious lot, private pool, and is close to downtown Sarasota and Siesta Key. Perfect for those seeking a tranquil lifestyle with easy access to amenities. Ideal for expansion or building your dream home.

Choice Landings location! This 3 bed, 3 bath home features a spacious great room, updated chef's kitchen, and a glassed-in lanai extending the living area. Enjoy a resurfaced pool, paver deck, and preserve views. The master suite boasts expansive sliders opening to the lanai. A split floor plan offers privacy for guest bedrooms. The community offers optional membership to the Racquet Club.

Luxury 4-bed, 3.5-bath pool home in Siesta Key. Modern West Indies style, 3630 sq ft, 10200 sq ft lot. Gourmet kitchen, office, wine room, saltwater pool, outdoor kitchen, 2-car garage w/storage. Move-in ready!

Damaged home sold for land value, solid structure, roof (2011), impact windows (2017). Water access, close to Siesta Key Village shops, restaurants, and beach. Ideal investment property for travelers. Serene location on a quiet street. Seller financing considered.

Build your dream home on this Siesta Key lot, just blocks from the beach! Previously damaged home and guest cottage sold for land value. Perfect for a full-time residence or vacation retreat. Close to shops and restaurants.

Fantastic canal-front lot (0.32 acres) in Sarasota, perfect for building a dream home. Short bike ride to Siesta Key beach. No HOA or CDD fees. Being sold as-is, cash transaction required.

Build your dream home on this Siesta Key lot, just two blocks from Siesta Beach! This property offers a prime location near the beach and village, perfect for a full-time residence or vacation retreat. Previously damaged structures are being sold for land value.

Presenting a unique restoration or new build opportunity on Siesta Key! This 3 bed, 2 bath home sits on a large lot, moments from the beach. Features a new 2024 roof & updated plumbing. Ideal for a primary residence or vacation retreat.

Oversized canal lot (.43 acres) in Siesta Key's Harmony subdivision. Features 80ft canal frontage, a composite dock, renovated pool, new windows/doors, and a full solar system. Sold as-is due to storm damage, offering remodel or new build potential. Near Siesta Village.