258 houses for sale in Cherokee Park, Sarasota city Sarasota CCD Sarasota County Florida

Welcome back to 648 Beach Road, youve seen it before, but its better than ever. Reconstructed, reimagined, and elevated in every detail, this extraordinary residence delivers the same breathtaking, front-row views you remember with an entirely new feel thats fresh, refined, and built for the way you live now. This expansive three-bedroom retreat lives like a private resort, with the space to convert to a five-bedroom, perfect for hosting, creating office space, or adding guest suites without sacrificing flow. Step outside to a wraparound terrace on every floor, designed for sunrise coffees, sunset cocktails, and everything in between, because when your backdrop is this spectacular, indoor/outdoor living isnt a feature, its a lifestyle. Ride your private elevator to the top and discover the ultimate luxury: a private rooftop pool where the horizon becomes your daily view and the sky feels like it belongs to you. Add in a rare four-car garage, and you have a true coastal statement home,

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

Virtually Staged. Exceptional West of Trail location! Nestled on a quiet cul-de-sac, this beautifully updated home offers the perfect blend of modern style and everyday comfort in one of Sarasota's most sought-after neighborhoods. Renovated throughout with tasteful finishes, the bright, open living spaces are designed for effortless living and entertaining. Enjoy a private backyard with room to relax, play, or entertain. Located outside of a flood zone and just minutes from Southside Village, Siesta Key Beach, downtown Sarasota, Sarasota Memorial Hospital, top-rated schools, shopping, dining, and waterfront parks. A rare opportunity to own a move-in ready home in an unbeatable location with easy access to everything Sarasota has to offer

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

Why spend 30–45 minutes idling through canals when you can reach sarasota bay in less than 3 minutes? Offering the fastest open-water access currently available on Siesta Key under $2.5 million, this exceptional waterfront residence delivers approximately 95 feet of waterfront, a 75-foot dock and a premier deep-water canal location designed for serious boating enthusiasts. If you’ve been searching for a waterfront home that prioritizes boating convenience over lengthy canal runs, this is one of the most compelling opportunities currently available on Siesta Key. Positioned on one of the island’s premier deep-water canals, the property offers the rare combination of protected dockage and near-immediate access to open water. Whether you’re heading offshore, cruising the Intracoastal or enjoying a sunset cruise across Sarasota Bay, this location delivers a level of boating convenience few waterfront properties can match. Boater highlights include less than three minutes to Sarasota Bay, a

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

Nestled in the heart of Sarasota, Florida, The Seathrough House' stands as a testament to timeless elegance and modern sophistication. Designed by the acclaimed architectural firm Sweet Sparkman and meticulously crafted by builder Josh Wynne, this mid-century marvel redefines luxury living. From the moment you step inside, the panoramic bay views captivate the senses, seamlessly blending the indoors with the breathtaking natural beauty of the surroundings. Every room boasts expansive windows, offering an uninterrupted vista of Sarasota Bay that is nothing short of mesmerizing. This architectural masterpiece features five bedrooms and five baths, providing ample space for both relaxation and entertaining. Each room is thoughtfully designed to maximize comfort and functionality while showcasing the stunning waterfront backdrop. Situated'West of the Trail, this premier location places you just minutes away from the world-renowned Siesta Beach, downtown Sarasota, and the charming Southside

Find your sanctuary in this exquisite Allegra custom home, ideally located on one of the few non-throughfare streets in the highly coveted West of the Trail neighborhood. Serene and understated from the outside, the home opens to a breathtaking entry that reveals an extraordinary Great Room featuring soaring 21-foot beamed ceilings, a dramatic windowed rotunda, and an open-concept design bathed in natural light. Oversized 10-foot doors frame every room, while hurricane-impact sliding glass doors seamlessly connect the interior to a resort-style outdoor oasis. The expansive pool deck showcases a stunning lighted fountain spilling from the spa into the oversized pool, a rainfall pergola, and lush tropical landscaping surrounded by a six-foot privacy fence—creating the ultimate setting for both relaxation and entertaining. Built with the signature craftsmanship of Allegra Homes, the residence features exceptional custom millwork, striking feature walls, designer lighting, and distinctive

Situated amongst the natural beauty of Bevena Pines, this gorgeous home awaits! Centrally located, this home is just minutes to the beaches of Siesta Key, Legacy bike trail, and Red Bug Slough with fishing dock, and play and picnic area. The home itself is located in a quiet cul de sac and the huge, welcoming oak tree is a perfect shade and climbing tree! Wonderfully updated inside, this split floorplan offers multiple spaces including living room, family room, informal and formal dining spaces. Great for entertaining! The large primary bedroom includes a massive walk-in closet, and private bath with double sink and clawfoot tub. Numerous skylights throughout for lots of natural light. Two additional large bedrooms on the other side of the home! The updated kitchen features a double convection oven, granite countertops and large breakfast bar! The screened porch let's you enjoy your Florida weather and more

Why spend 30–45 minutes idling through canals when you can reach sarasota bay in less than 3 minutes? Offering the fastest open-water access currently available on Siesta Key under $2.5 million, this exceptional waterfront residence delivers approximately 95 feet of waterfront, a 75-foot dock and a premier deep-water canal location designed for serious boating enthusiasts. If you’ve been searching for a waterfront home that prioritizes boating convenience over lengthy canal runs, this is one of the most compelling opportunities currently available on Siesta Key. Positioned on one of the island’s premier deep-water canals, the property offers the rare combination of protected dockage and near-immediate access to open water. Whether you’re heading offshore, cruising the Intracoastal or enjoying a sunset cruise across Sarasota Bay, this location delivers a level of boating convenience few waterfront properties can match. Boater highlights include less than three minutes to Sarasota Bay, a

Welcome to your dream home on Lido Key! This impressive 3-story residence offers a luxurious living experience with breathtaking water views from its private rooftop oasis. With 6 bedrooms, 6 full bathrooms, and 2 half-bathrooms spread across 3,914 square feet, this home is a masterpiece of modern design, boasting sleek clean lines, abundant natural light, and high-end finishes throughout. As you step into the grand entrance on the main floor, you'll be captivated by the open-concept layout and the panoramic wall-to-wall windows that showcase the stunning living, dining, and gourmet kitchen areas. The kitchen is a chef's delight, featuring stylish pendant lighting, gold accents, a massive island with a waterfall quartz countertop, and herringbone wood tile flooring. Top-of-the-line stainless steel appliances, double ovens, and elegant fixtures complete the sleek design. This home offers multiple dining options, perfect for entertaining. The open-concept dining area is ideal for indoor

Experience the epitome of luxury with this stunning home that defines coastal elegance. Nestled on a quiet island street, this Florida Coastal masterpiece is set on a large 12,805 square foot lot with 75 ft of private lakefront overlooking the serene waters of Lake Norma, on our famed Siesta Key. Renovated with meticulous attention to detail, this newly updated home features an expansive, light-filled open floor plan with continuous quartzite countertops throughout. It includes two primary suites, one of which flows into its own private kitchenette overlooking the tranquil waterfront. Two lanais and a custom built hot tub and pool complete with a waterfall and color-changing lighting system ensure seamless indoor-outdoor living. Quality and craftsmanship are paramount, and every detail has been thoughtfully considered to ensure superior structural integrity, including the hurricane impact windows and elevated AC condensers. A new roof was installed in 2024, along with new mechanicals,

Welcome to your dream island retreat, perfectly nestled in the heart of Siesta Keys Palm Island, just minutes away from the world-famous Siesta Beach and vibrant Siesta Village. This beautifully renovated 4-bedroom, 4-bathroom home is the epitome of coastal luxury, offering the ultimate island lifestyle where you can enjoy sun, sand, and all the amenities of this exclusive locale. Meticulously transformed by the renowned Nautilus Homes, this home boasts an open floor plan with soaring high ceilings, making it the perfect space for both relaxation and entertaining. Every inch of the property has been updated with the finest finishes and state-of-the-art features, including: Gourmet Kitchen with new appliances, Impact-Resistant Windows for peace of mind, New 17KW Solar System with backup generator, keeping your electric bill at an incredibly low $20-$30 month, New Boat Lift Motors and a private dock, perfect for boating enthusiasts, Saltwater Pool System and spa, enclosed in a serene, wa

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

Under contract-accepting backup offers. Experience the ultimate in coastal luxury with this exceptional waterfront residence on Lido Key. Perfectly positioned along a wide, private deep-water canal, this beautifully renovated 3-bedroom, 3.5-bath home offers direct, bridge-free boating access to the Intracoastal Waterway and the Gulf of Mexicoan extraordinary feature for boating enthusiasts. Just two blocks from pristine Lido Beach and within walking distance to the vibrant shops and restaurants of St. Armands Circle, this home combines an unbeatable location with a serene, private setting. Designed to maximize its stunning waterfront surroundings, the home features expansive living spaces with six sets of sliding glass doors that seamlessly blend indoor and outdoor living. Step outside to a screened-in, south-facing heated pool and spacious paver deckideal for entertaining or simply relaxing while enjoying tranquil canal views. The private dock 2024 is fully equipped with a lift, power

2 buildable waterfront lots. Palm Island IS the'Heart of Siesta Key'. Don't miss this rare opportunity to live in Siesta Key's most sought-after neighborhood and experience the quiet, friendly, yet close to everything community of Palm Island. Build your tropical dream home on one lot and sell the other, or go'all in' and create your ideal island estate on the 17,883 sq ft lot. If restoration is more your style, this home was built using the Lamolithic poured in place construction method developed by John Lambie Jr and was a key design element in the Sarasota School of Architecture. As a result, most of the primary structure and walls are made of 12 inch poured concrete, providing unsurpassed strength and durability. This spacious property located in one of the finest and friendliest communities on Siesta Key is situated a mere 600 feet from arguably the best beach on the planet. Situated on the Grand Canal, it is minutes by boat to the Intercoastal Waterway and a short walk or bike ri

Sarasota. City of sarasota. Rosemary district. Downtown living and / or investment, with upside development opportunities! We are selling 4 contiguous properties with four rental homes on an estimated 23k sf +/. Land! Come and explore this unique opportunity to own and operate four contiguous properties with homes within the much sought after City of Sarasota'Rosemary District'. The current rent roll is estimated at $100K +/-, all the current homes (4) are rented on an annual basis. The zoning does allow for short term weekly rentals, come and set up your own short term rental compound with estimated average daily rates @ $50.00. 100.00 +/. Want another reason to look, owner will consider'owner financing' and/or selling off less then all four homes. There are just not many opportunities in the City of Sarasota to secure rezoned lands with the ability to use the current as-is property to secure carry income while waiting for the right timing to develop. The upside development in the Ros

For Those Who See Home as an Expression of Art. 541 S Washington offers a rare blend of architectural character, quality craftsmanship, and waterfront living. Beautifully renovated to reflect the enduring principles of Mid-Century Modern design, where clean lines, natural light, and a connection to the outdoors shape the living experience. Set on 75 feet of canal frontage along prestigious South Washington Drive, just moments from St. Armands Circle, Lido Beach, and downtown Sarasota. From the moment you enter, expansive folding glass doors frame the water beyond. A striking gas fireplace anchors the main living spaces, while thoughtfully proportioned rooms balance openness with comfort. Offering four bedrooms, four-and-a-half baths, and a flexible bonus space, the 3,395-square-foot floor plan was designed for easy every day living. At the center of the home, a custom Poliform kitchen with premium Miele appliances combines clean design with exceptional functionality. The primary suite

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