Homes For Sale in Sarasota 34239 - 230 homes

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: Under contract-accepting backup offers. 7 Rentable Units | 10 Bed, 8 Bath Income Property – Prime Siesta Key Location! Exceptional opportunity to own a fully leased multifamily property just minutes from world-famous Siesta Key Beach. Located on Siesta Drive—the gateway to Siesta Key—this offering includes two adjacent triplexes on two separate lots, with potential to expand to 8 units. The property features a versatile mix of 1BR, 2BR, 3BR, and studio layouts, ideal for maximizing rental income. Zoned for weekly rentals (7-day minimum) within city limits, this property offers strong income potential with a blend of long-term tenants and proven short-term rental performance (Airbnb 5-star host/seasonal). Recent upgrades include newer roofs (2016–2017), new siding, updated A/C units, hot water heaters (2021+), appliances, exterior plumbing, fencing, and security lighting/cameras. Professionally landscaped grounds enhance curb appeal. On-site laundry with the ability to add laundry to every unit. Tenants pay utilities with 7 separate water and electric meters. Situated just blocks from the North Bridge and within walking distance to shopping, dining, and everyday conveniences. Located in an X flood zone – NO flood insurance required, and Level D evacuation zone. Ample parking for up to 17 vehicles, plus space for boats, kayaks, and recreational toys. Buy one or both – must be sold simultaneously: 1761 Siesta Dr & 1760 Wisconsin Ln – a rare high-income investment package on Siesta Key. Strong financials: ~5.19% cap rate, under $20K in annual expenses, and projected income of $175K+ with upside potential. Do not disturb tenants. Showings by appointment only; listing agent must accompany all showings.

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

Listing Agent: Danielle Dietrich, Pa (603-767-9166)

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: Under contract-accepting backup offers. Siesta Key Triplex – Weekly Rental Zoned Investment Opportunity Concrete triplex in city limits featuring one 3BR/1BA unit with attached 1BR/1BA studio and two additional 1BR/1BA units. ALL units are tenant-occupied with immediate income potential; historical annual income reported at $80K–$100K. Zoned for weekly rentals in Siesta Key City Limits...allow short- or long-term rental flexibility. Property includes four electric and four water meters, with tenants paying utilities. Expenses are kept low and are primarily limited to taxes, insurance, and landscaping. Recent updates include A/C systems, water heaters, appliances, exterior lighting, security cameras, and landscaping. Features shared on-site laundry plus private laundry in the larger unit. Concrete construction makes this the perfect investment property close to the beach and in Evacuation Zone D. No flood insurance required! Prime location near Siesta Key Beach with easy access to shopping, dining, and public transportation. Approximately two blocks to the North Bridge. Add 1761 Siesta Dr to increase your income potential and begin your Siesta Key Portfolio or scale to a 7+ unit portfolio with a potential six-figure+ income gain. Why buy just one when you can buy both! Strong in-place income makes this a rare Siesta Key investment. Intended to be sold together. Do not disturb tenants. Showings by appointment only; listing agent must accompany all showings.

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

Listing Agent: Danielle Dietrich, Pa (603-767-9166)

Remarks: Under contract-accepting backup offers. Siesta Key Triplex – High-Yield, Weekly Rental Zoned Investment! Concrete triplex in city limits featuring one 2BR/2BA and two 1BR/1BA units with long-term tenants in place...immediate cash flow from day one. Proven income of $65K–$85K annually with low overhead expenses (taxes, insurance, landscaping only). Tenants pay all utilities with separate electric & water meters for each unit. Weekly rental zoning in city limits is a major upside for short-term income potential. Ideal for investors looking to significantly increase returns or house-hack by living in one unit and renting the others. Recent upgrades include new A/C systems, water heaters, appliances, security cameras, exterior lighting, and tropical landscaping. Solid concrete construction in Evacuation Zone D and NO flood insurance is required. Prime location just minutes to Siesta Key Beach, walking distance to dining, shopping, and essentials. Quick access on/off the key only 2 blocks to North Bridge. Value-add opportunity: Purchase adjacent property at 1760 Wisconsin Lane to scale to a 7+ unit portfolio with potential six-figure+ income. Why buy just one when you can buy both! Strong in-place income makes this a rare Siesta Key investment. Do not disturb tenants. Showings by appointment only; listing agent must accompany all showings.

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

Listing Agent: Danielle Dietrich, Pa (603-767-9166)

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: One or more photo(s) has been virtually staged. Fully renovated Southgate home, set on a spacious, tree-lined corner lot. Ideally located just minutes from Siesta Key Beach, St. Armands Circle, and vibrant downtown Sarasota. Step inside to an open, light-filled layout designed for both comfort and entertaining. This 3-bedroom, 3-bathroom home features a desirable split floor plan, providing privacy for family and guests alike, along with a fenced backyard perfect for relaxing or hosting gatherings. The main bedroom is a true retreat, complete with a walk-in closet and a beautifully updated en-suite bathroom featuring a modern walk-in shower. Two additional bedrooms and full bathrooms complement the home—offering flexibility and convenience for family and guests. The interior showcases brand-new flooring and a beautifully updated kitchen equipped with sleek stainless steel appliances, elegant stone countertops, and a striking island with a suspended exhaust hood—perfect for those who love to cook and entertain. Designer lighting throughout adds a refined, modern touch. The spacious living area centers around a cozy wood-burning fireplace, creating a warm and inviting atmosphere that truly feels like home. This is a rare opportunity to own a move-in-ready home in one of Sarasota’s most desirable locations.

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Christine Landrau (407-949-1421)

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)

Remarks: Investor / Builder Alert! Exceptional WEST OF TRAIL opportunity in one of Sarasota’s desirable neighborhoods, Poinsettia Park. Located just steps from top-rated Southside Elementary School, this property offers incredible potential for redevelopment. The existing structure is a grandfathered duplex that is in very poor condition and best suited for teardown. The true value lies in the land — a 50’ x 118’ lot ideally positioned for a stunning new custom home. Enjoy a highly sought-after location just minutes to the shops and dining of Southside Village, the world-renowned beaches of Siesta Key, and the vibrant arts, dining, and waterfront lifestyle of Downtown Sarasota. Whether you’re a builder, investor, or end user looking to create a dream home, this is a rare chance to build new in an established, high-demand area surrounded by luxury properties. Opportunities like this are becoming increasingly scarce—don’t miss your chance to capitalize on this premium location!

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

Listing Agent: Ryan Carson (941-685-2879)

Remarks: Presenting a distinguished waterfront estate located in Sarasota’s premier bayfront community, Harbor Acres, widely regarded as the city’s most coveted neighborhood. Perfectly situated on a protected deep-water boat basin, this property offers immediate access to Sarasota Bay with the added benefit of a boat dock and lift on calm waters-ideal for larger vessels. With prized southern rear exposure, the home is bathed in natural light throughout the day, while capturing glowing sunsets across the water — a rare and highly desirable feature for waterfront living. The thoughtfully designed 4-bedroom, 6 bath floor plan offers exceptional flexibility and privacy, with distinct guest wings that function almost as private suites — ideal for hosting extended family, visiting friends, or even live-in arrangements without sacrificing personal space. The seamless flow between formal and casual living areas makes the home equally suited for elegant entertaining or relaxed everyday living. At the heart of the home, the chef’s kitchen features beautiful quartz countertops, island, abundant cabinetry, and premium appliances, opening effortlessly to the family room and outdoor living areas. A striking double-sided gas fireplace creates ambiance between key gathering spaces, enhancing both intimate evenings and larger gatherings. Enjoy the rare luxury of choosing between two primary suites. Both primary suites are serene retreats offering generous proportions, tranquil water views, and a spacious walk-in closets with custom built-ins designed for optimal organization. The spa-inspired baths provides a luxurious escape at the end of the day. Outdoor living is where this property truly shines. A fully equipped summer kitchen anchors the covered lanai, creating the perfect setting for waterfront dining and entertaining. The infinity edge pool, spa and outdoor lounge areas overlook the wide boat basin, where you can watch dolphins pass and boats glide by — all from the comfort of your own backyard.

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

Listing Agent: Kim Ogilvie (941-951-6660)

Remarks: Introducing “Gatsby Manor,” set along Hillview Drive, one of Sarasota’s most coveted bayfront addresses, often compared to Port Royal for its exclusivity and waterfront lifestyle, this rare Harbor Acres estate property spans nearly three-quarters of an acre on deep, boatable water with sweeping, unobstructed Sarasota Bay views stretching south toward Siesta Key and the Gulf of Mexico, representing one of the neighborhood’s most distinguished open-bay offerings where only a select few residences achieve true estate scale. Encompassing more than 8,000 square feet of air-conditioned space with four bedrooms and three-and-a-half baths. The residence is complemented by a grand motor court accommodating 15+ vehicles beneath a canopy of majestic grand oaks. Privately approached through wrought-iron gates and a sweeping circular drive anchored by a multi-tiered fountain, the home opens to a dramatic two-story foyer framing the water beyond. Interiors are defined by soaring ceilings up to 22 ft. in height, exceptional millwork, multiple fireplaces, a striking two-story wood-paneled library, formal dining with 12-foot ceilings, and a wetbar—perfectly blending elegant entertaining with comfortable daily living. The chef’s kitchen is designed to support both everyday living and large-scale gatherings, featuring double 36-inch Sub-Zero refrigerators with dual freezer drawers, two dishwashers, and a 60-inch Wolf gas range with six burners and infrared dual griddle. The owner’s suite occupies the entire east wing of the main living level, creating a private waterfront retreat complete with a gas fireplace, sitting area overlooking the pool and bay, dual walk-in closets, and a spa-inspired bath highlighted by a sculptural copper soaking tub, dual vanities, and a dedicated luxury makeup area. Upstairs, a second primary-style suite and two additional guest bedrooms are accessed via the grand staircase or three-stop elevator, offering privacy and flexibility for family and guests. The 3,800+ square-foot ground-level bonus area serves as the home’s ultimate entertaining environment, featuring a remarkable speakeasy lounge and an impressive 700+ bottle wine room. This expansive space functions as a true extension of the residence’s living experience—ideal for hosting gatherings, intimate evenings, or celebrations on a grand scale. Outdoor living is equally exceptional, centered around an expansive marble terrace surrounding the 25’ × 60’ heated saltwater pool with integrated sun shelf and spa. A brand new deep-water dock with a 20,000 lb. boat lift and seawall replaced in 2017 further enhance the property’s boating capabilities and long-term value. Additional highlights include hurricane-rated garage doors, elevator access to all three levels, a drive-through three-car garage, and extensive storage throughout. Perfectly positioned just a short stroll to Southside Village’s restaurants and boutiques, minutes from downtown Sarasota’s celebrated arts and cultural district, and only four blocks from Sarasota Memorial Hospital. Gatsby Manor offers a truly rare opportunity to enjoy estate-scale open-bay living with deep water, privacy, and exceptional walkability in one of Sarasota’s most prestigious waterfront neighborhoods.

Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)

Listing Agent: Ryan Ackerman, Pa (305-205-7700)

Remarks: Anchored in one of Sarasota’s most coveted deep water waterfront communities, 3631 San Remo Terrace presents a rare opportunity to own a modern luxury home with direct boating access in San Remo Estates, just moments from Siesta Key, Downtown Sarasota, and Southside Village. Completed in 2021 by award-winning designer Stephen Chung and enhanced with thoughtful 2025 upgrades, this coastal contemporary residence blends clean architectural lines with warm, natural finishes, ideal for buyers seeking newer construction, move-in-ready condition, and hurricane-resilient design in a prime location. Positioned on protected sailboat water with no fixed bridges, the property offers seamless access to Sarasota Bay and a short, unobstructed ride to the Gulf, making it perfectly suited for avid boaters. Spanning approximately 4,750 square feet under air, with nearly 3,000 additional square feet of outdoor living space, the home is designed around the indoor-outdoor lifestyle today’s luxury buyers prioritize. The open-concept layout is anchored by a chef’s kitchen featuring a sculptural marble island and Sub-Zero and Wolf appliances, flowing effortlessly into a great light-filled room with a stone fireplace, custom built-ins, and floor-to-ceiling glass sliders that open to expansive terraces. A temperature-controlled wine room with 1,800-bottle capacity adds a refined touch, while the dining space creates a striking architectural focal point. The primary suite offers true resort-style living, with private access to both a tranquil courtyard with spa and sauna and the waterfront pool terrace. Inside, a custom walk-in closet and spa-inspired bath reflect the level of finish expected in a luxury retreat. The second level features three additional bedrooms, a flexible gym or office, and a loft-style workspace, providing versatility for modern living. Outdoors, the illuminated saltwater pool with a glass wall, newly enhanced outdoor kitchen, and expansive entertaining areas create a private waterfront oasis. The deep-water dock is equipped with a 20,000-pound boat lift, dual jet ski lifts, and a floating dock, delivering a true boating lifestyle. Additional highlights include a three-car garage with a lift, epoxy flooring, and custom storage. A fully integrated smart home system, featuring programmable lighting and shades, whole-home audio, Apple TV integration, a generator, and high-speed WiFi, meets the expectations of today’s tech-forward buyer. Furniture is available separately to create a more turnkey concept. Located within San Remo Estates, the home offers a rare balance of privacy and central convenience. Just minutes from Siesta Key via the nearby North Bridge, beach access becomes part of everyday life. Set on a deep-water basin seconds from Sarasota Bay, the property provides protected docking with immediate access to open water and a short ride to the Gulf. Southside Village and Downtown Sarasota are both a quick drive away without the need to cross any bridges, offering boutique shopping, cafés, acclaimed dining, and a vibrant arts and cultural scene. Everyday conveniences, including top-rated schools, Sarasota Memorial Hospital, and key corridors like US-41 and I-75, are all within close reach. This is a location that seamlessly connects protected waterfront living with the very best of Sarasota.

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

Listing Agent: Joel Schemmel (941-587-4894)

Remarks: MAJOR PRICE REDUCTION - MUST SEE! This gorgeous home in the iconic Rustic Lodge enclave in Arlington Park was meticulously remodeled in 2020. The thoughtfully designed layout flows seamlessly from a central gathering space combining great room and kitchen—ideal for everyday living and entertaining. Highlights include soaring shiplap ceilings, engineered hardwood floors, premium lighting, and PGT impact doors and windows. The kitchen is anchored by a large island featuring granite countertops, high-end appliances, and custom cabinetry, while French doors open to the secluded outdoor spaces. This 3 bed 2 bath split floor plan features a Primary Suite with elegantly appointed walk-in closet and a spa-inspired bathroom complete with walk-in shower, soaking tub, and dual sinks. The north wing of the home includes two guest bedrooms and a full bath with shower/tub combination, offering separation and privacy from the primary suite. Conveniently located adjacent to the kitchen, the laundry room includes a top tier washer and dryer. An oversized garage affords a full wall of built-in storage space. Outdoor features include a newly landscaped garden, decorative awnings, delightful garden art, a driveway with inset river rock, and a walled "secret garden" oasis in the side yard, complete with shade umbrella and charming garden gate. Major systems/appliances replaced during the total renovation in 2020 include roof, air conditioning, water heater, electrical, plumbing, kitchen, bathrooms, flooring, and impact resistant doors and windows. Ideally situated on a corner lot near the Arlington Park complex, and just minutes from Downtown Sarasota, Southside Village, and award winning Siesta Key Beaches.

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

Listing Agent: Carol-Ann Warr (941-780-0665)