Location: Sarasota , 34239
Do Not Show Listings
1959 HIBISCUS ST, SARASOTA, FL 34239
$2,395,000193 Days on yellowkey MLS ID: A4667271
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2720 Built: 2019 Tax: $22,649 (2025)Community: Desota ParkSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$22,649
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: PRICE IMPROVEMENT! An exceptional one-story Allegra home in Sarasota’s coveted West of Trail Flower Streets, perfectly positioned within the Southside School district and just steps from the charming Southside Village restaurants, shops, and Morton’s Gourmet Market. This impeccably designed 3-bedroom + office + bonus room, 2.5-bathroom home epitomizes modern coastal living and showcases the esteemed Kristi Ann single story floor plan, offering a seamless blend of sophisticated design and everyday functionality, making it an ideal primary or seasonal residence. Double doors open to the soaring 18-foot ceiling and wall of expansive 10-foot pocketing sliders which draw you towards the resort-like outdoor retreat, perfect for relaxing or entertaining. The living room features a dramatic floating tray ceiling with Halo-LED lighting and a focal wall complete with a remote-controlled electric fireplace. The chef's kitchen is functional and stylish, equipped with stainless steel appliances, a 5-burner gas range, Quartz island and countertops, and a generous walk-in pantry. The dining area, both intimate and elegant, includes a built-in Quartz-topped buffet, creating a serene space for family meals or hosting guests. The primary suite offers a tranquil escape, with vaulted ceiling accented by charming wood beams. The spacious custom walk-in closet ensures ample storage, while the spa-like en-suite bathroom, featuring glass-enclosed shower and designer tile, is the perfect respite after a long day. Two additional large guest bedrooms, along with a well-appointed guest bathroom and powder room, offer comfort and privacy for family or visitors. This award-winning floorplan also boasts a dedicated office, versatile bonus room, laundry room, and a 2-car AC'd garage with added storage. Step outside and discover an expansive lanai with a resort-style heated pool, spa, and impressive summer kitchen, all surrounded by lush landscaping and illuminated by custom lighting. The disappearing corner sliders seamlessly blend indoor and outdoor spaces, offering the quintessential Sarasota lifestyle. This home is packed with custom features, including designer lighting and built-ins, PGT impact windows, solid-core interior doors, and spray foam insulation for optimal energy efficiency. Recent upgrades include remote-controlled Kevlar shades for additional hurricane protection/storage for outside furnishings/sunshade, new AC unit with UV lights, 2023 mini split AC unit in the garage, and a whole-home in-duct air purifier. Ideally positioned near Southside School, Southside Village, Sarasota Memorial Hospital, Downtown Sarasota, and Siesta Key Beach, it delivers the ultimate blend of location, luxury, and lifestyle. Built to the latest hurricane codes and outside the flood zone, the home provides peace of mind along with timeless design. Every detail has been thoughtfully curated, creating an exceptional opportunity for discerning buyers to experience the best of Sarasota living in a true single-story gem.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lenore Treiman (941-356-9642)
1857 TULIP DR, SARASOTA, FL 34239
$2,650,00022 Days on yellowkey MLS ID: A4687590
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1878 Built: 1952 Tax: $11,355 (2025)Community: Hartland Park ResubSingle Family
Taxes:$11,355
Remarks: Modern coastal living in a prime West of the Trail location. This extensively renovated 3-bedroom, 2-bath residence offers nearly 1,900 square feet of bright, open living space with clean finishes and seamless indoor-outdoor flow. Renovations include updated systems, impact windows and doors, and a complete kitchen and bath redesign. The private pool with spa and swim shelf, along with upgraded exterior features, creates a relaxed and functional outdoor setting designed for low-maintenance living. Positioned in one of Sarasota’s most desirable neighborhoods, where new construction and continued demand continue to push values forward, this property captures both lifestyle and long-term potential. No HOA or rental restrictions provide flexibility for full-time use, seasonal enjoyment, or income potential. Currently operating as a successful luxury short-term rental. A standout opportunity in a location that continues to set the pace for Sarasota living.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Ralf Michael Guensch (941-350-3450)
1423 & 1435 HILLVIEW DR, SARASOTA, FL 34239
$17,350,000317 Days on yellowkey MLS ID: A4653958
Bed: 6 Bath: 8.0 Liv Area Sq Ft: 11588 Built: 2006Community: Harbor AcresSingle Family
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: Welcome to a home that lives like a resort, set on two lots consisting of 1.8 lush, waterfront acres in Sarasota’s premier neighborhood, Harbor Acres. Crafted for laid-back luxury and everyday ease, this nearly 12,000-square-foot estate offers 249 waterfront feet and is designed for entertaining, all set against views of Sarasota Bay, Ringling Causeway and the downtown skyline. An expansive paver driveway winds through mature palms to a stone exterior with travertine steps, a porte cochere and an expansive porch, all setting the tone for within. Solid wood doors open to a soaring foyer with wood columns, intricate millwork and custom archways that reflect the home’s detailed character. Designed for easy living, the main spaces flow effortlessly, highlighted by a family room with zero-corner sliders, a wall of windows overlooking the water, a coffered wood ceiling, and a stone fireplace that anchors the room. Detailed trim, crown molding, and wood wainscoting add depth and highlight craftsmanship throughout. The kitchen is anchored by a large island with storage, prep space and a sink, and equipped with top-tier appliances including Dacor double ovens and range, Sub-Zero refrigerator and freezer, dual Bosch dishwashers, a warming drawer and a Scottsman ice maker. A walk-in pantry with custom shelving keeps everything organized, while the adjacent butler’s or catering kitchen—with its own cooktop, refrigerator, microwave and desk area—makes entertaining easy. An eat-in area with an aquarium window and bar-height counter seating keeps it functional and inviting. A wine room with wood-paneled walls and a separate entertaining bar with an oversized wine cooler make this home ideal for gatherings of any scale. The theatre offers the ultimate at-home viewing experience with custom wall and ceiling treatments, tiered seating, blackout glass windows and door, and a built-in bar with sink and more seating, ideal for movie nights, game days or entertaining. Outside is an extension of the home’s lifestyle, offering resort-style features meant for everyday use. The pool features a sun shelf, stone accents, and cascading water features paired with a raised spa, while the outdoor kitchen, with grill, refrigerator and bar seating, makes entertaining effortless. A dedicated pool bath adds convenience, and nearby, the turf yard, fire pit and hammock invite easy relaxation. A spiral staircase connects the primary suite terrace to it all, while a versatile sport court and two private docks for 75-plus-foot yachts complete the experience. Back inside, the home offers a thoughtful blend of privacy and flexibility. The primary suite is a retreat with incredible views, French doors to a private terrace, a coffee bar and a sitting room with a fireplace. Its spa-inspired bath features a jetted tub, multi-head shower, custom dual vanity and dual walk-in closets. A separate in-law suite provides full independence with its kitchenette, living room, laundry and terrace. Guests enjoy four more suites with private baths, a bonus room with a terrace, a fitness room, a built-in homework area, and easy access across all levels via dual staircases and a three-stop elevator. Abundant garage and storage space complete the estate. This Harbor Acres home delivers the ultimate Sarasota lifestyle, just minutes from downtown, Southside Village and Gulf beaches. The vacant lot at 1435 Hillview can be separated and the list price reduced accordingly.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
1423 HILLVIEW DR, SARASOTA, FL 34239
$13,900,00028 Days on yellowkey MLS ID: A4686188
Remarks: Welcome to a home that lives like a resort in Sarasota’s premier neighborhood, Harbor Acres. With 134 feet of water, this nearly 12,000-square-foot estate is crafted for laid-back luxury and everyday ease, designed for entertaining against breathtaking views of Sarasota Bay, the Ringling Causeway, and the downtown skyline. A paver driveway winds through mature palms to a stone exterior with travertine steps, a porte cochere, and an expansive porch, all setting the tone for within. Solid wood doors open to a soaring foyer with wood columns, intricate millwork, and custom archways that reflect the home’s detailed character. Designed for easy living, the main spaces flow effortlessly, highlighted by a family room with zero-corner sliders, a wall of windows overlooking the water, a coffered wood ceiling, and a stone fireplace that anchors the room. Detailed trim, crown molding, and wood wainscoting add depth and highlight craftsmanship throughout. The kitchen is anchored by a large island with storage, prep space, and a sink, and equipped with top-tier appliances including Dacor double ovens and range, Sub-Zero refrigerator and freezer, dual Bosch dishwashers, a warming drawer, and a Scottsman ice maker. A walk-in pantry with custom shelving keeps everything organized, while the adjacent butler’s or catering kitchen, with its own cooktop, refrigerator, microwave, and desk area, makes entertaining effortless. An eat-in area with an aquarium window and bar-height counter seating keeps it functional and inviting. A wine room with wood-paneled walls and a separate entertaining bar with an oversized wine cooler make this home ideal for gatherings of any scale. The theatre offers the ultimate at-home viewing experience with custom wall and ceiling treatments, tiered seating, blackout glass windows and door, and a built-in bar with sink and additional seating. Outside is an extension of the home’s lifestyle, offering resort-style features meant for everyday use. The pool features a sun shelf, stone accents, and cascading water features paired with a raised spa, while the outdoor kitchen, with grill, refrigerator, and bar seating, makes entertaining effortless. A dedicated pool bath adds convenience, and nearby, the turf yard, fire pit, and hammock invite easy relaxation. A spiral staircase connects the primary suite terrace to the outdoor amenities, and a private dock completes the experience. Back inside, the home offers a thoughtful blend of privacy and flexibility. The primary suite is a retreat with incredible views, French doors to a private terrace, a coffee bar, and a sitting room with a fireplace. Its spa-inspired bath features a jetted tub, multi-head shower, custom dual vanity, and dual walk-in closets. A separate in-law suite provides full independence with its kitchenette, living room, laundry, and terrace. Guests enjoy four additional suites with private baths, a bonus room with a terrace, a fitness room, a built-in homework area, and easy access across all levels via dual staircases and a three-stop elevator. Abundant garage and storage space complete the estate. This Harbor Acres residence delivers the ultimate Sarasota lifestyle, just minutes from downtown, Southside Village, and Gulf beaches. The adjacent vacant lot at 1435 Hillview is currently offered separately, with the opportunity to purchase both together. Bank signoff on the sale of this property may be required. The gate and driveway would need to be reconfigured.
1704 WISCONSIN LN, SARASOTA, FL 34239
$625,00053 Days on yellowkey MLS ID: A4683524
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 700 Built: 1959Community: BayviewSingle Family
Remarks: Welcome to your perfect coastal escape—an inviting cottage offering charm, comfort, and an ideal location away from the hustle and bustle of city life. Just a few miles from Siesta Key Beach, you’re only a short bike or golf cart ride from the world-famous quartz sand shores. This beautifully renovated two-bedroom, one-bath home has been thoughtfully updated from top to bottom. Inside, you’ll find a warm and welcoming layout, while outside, a spacious screened lanai provides the perfect spot to relax and unwind. There’s also ample outdoor space designed for easy Florida living. Located on Wisconsin Lane just off the north Siesta Key Bridge, this property offers convenient access to the shops and restaurants of Southside Village, placing dining, entertainment, and everyday essentials within easy reach. Whether you’re searching for a serene winter retreat, a smart investment opportunity, or a comfortable in-law residence in a safe and highly desirable neighborhood, this prime location checks all the boxes. After a long day at the beach, come home to your private haven and relax in style.The low-maintenance landscape design features elegant stone and shell accents, complemented by irrigation and ambient landscape lighting throughout the property. Don’t miss your opportunity to own this exceptional cottage—schedule your private showing today!
Listing is courtesy of: MCCONNELL AND ASSOCIATES (941-539-1916)
Listing Agent: Oliver Mcconnell (941-539-1916)
3372 WEBBER ST, SARASOTA, FL 34239
$399,00049 Days on yellowkey MLS ID: W7883327
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1869 Built: 1961Community: South Gate ManorSingle Family
Remarks: Welcome to this spacious 4-bedroom, 2-bath home with a large bonus room / second living area, perfectly designed for families who need room to grow — or multigenerational living. This almost 1900 square footage beauty offers a flexible layout with separate living spaces, making it easy to create an in-law setup, teen retreat, playroom, or home office wing. Inside, you’ll find beautiful plaster ceiling work, high-end Italian cabinetry, with thoughtful updates, preserving charming retro details like the original pink subway tile bathroom and preserved mosaic tile in a few featured room— a rare blend of character and comfort. Step outside to enjoy a large porch and private-feeling yard shaded by mature trees, ideal for gatherings, playtime, or quiet evenings at home. This home is built to weather storms with an updated metal roof, built with concrete block and a beautiful brick front and seating area. There is a garage, laundry and a massive amount of parking. AC was recently updated. Centrally located yet surprisingly peaceful, this home is minutes to downtown and beaches and sits in a high-and-dry area, flood-zone X, for added peace of mind. If you’ve been searching for space, flexibility, major upgrades already complete, and timeless charm in one place — this is it.
Listing is courtesy of: SIMPLE FEE LISTINGS LLC (734-674-6608)
Listing Agent: Randall Wolber, Jr (734-674-6608)
1610 S ORANGE AVE, SARASOTA, FL 34239
$1,625,00023 Days on yellowkey MLS ID: A4687305
0 Days Off yellowkey (back on 3/25/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2193 Built: 1969Community: Harbor AcresSingle Family
Remarks: Charming Harbor Acres 3 bedroom, 2 bath home on a beautifully landscaped lot offering privacy and convenience in one of Sarasota's most desirable West of Trail neighborhoods. A circular driveway framed by mature palms and lush Florida foliage leads to a light-filled interior with plantation shutters, crown molding, and a mix of tile and hardwood floors. The open floor plan flows seamlessly between living, dining, and kitchen areas ideal for daily living and casual entertaining. Enjoy a fully screened lanai that encircles the heated pool and spa, set on natural stone pavers. Surrounded by lush tropical landscaping, the backyard offers a serene, private retreat.
Listing Agent: Barbara May (404-822-9264)
3000 SOUTHWEST DR, SARASOTA, FL 34239
$13,250,000144 Days on yellowkey MLS ID: A4672971
Bed: 5 Bath: 5.5 Liv Area Sq Ft: 8125 Built: 2003Community: Cherokee ParkSingle Family
Remarks: One of Sarasota’s greatest bayfront estates, this stunning 1.38 acre waterfront home has recently undergone a comprehensive renovation throughout, enhancing every room with refined finishes and modern systems while preserving its timeless architectural character. Hidden away at the end of Southwest Drive within the coveted Cherokee Park neighborhood, this 5-bedroom home offers exceptional seclusion and privacy, surrounded by lush, verdant landscaping, specimen trees and mature oaks, with tranquil water views providing a serene backdrop throughout the entire home. A masterpiece by design, this architectural gem was designed by esteemed architect Clifford Scholtz and built with impeccable craftsmanship by Rich Perrone of Perrone Construction. Among the recent exterior improvements are a new roof and gutters, fresh exterior paint, new decorative landscape lighting, and a refreshed outdoor shower. Inside, thoughtfully curated modern finishes and updates seamlessly blend with classic architectural details such as columns, archways, and a mahogany-paneled office, creating interiors that feel bright, open, and timeless. New European white oak flooring flows through the main living areas, while Stark carpeting adds warmth to the staircase, select bedrooms, and the bonus room. A culinary enthusiast’s dream, the completely updated kitchen boasts Taj Mahal leathered stone countertops, White Haze dolomite backsplash, a micro cement hood, painted cabinetry, an oversized island, new sinks and faucets, a Sub-Zero fridge/freezer, and more. The charming breakfast area and adjacent family room, featuring a new micro cement fireplace with Taj Mahal hearth, are set against a backdrop of expansive windows and glass doors that capture picturesque bay views. A luxurious and peaceful retreat, the elaborate primary suite features a beautifully updated bath showcasing new vanities with Taj Mahal countertops and Brizo fixtures, plus new flooring, soaking tub, and walk-in shower. Secondary baths throughout the home have also been refreshed. Covered patios and loggias extend from the main living areas, creating ideal spaces for relaxation and enjoyment. Upstairs, the expansive gathering room impresses with its custom Perla Venata quartzite bar, freshly painted ceiling beams, large windows, and balcony access overlooking the bay, pool, and lush grounds. This is the perfect perch to enjoy large gatherings, relax at the bar, shoot pool, or have friends and family over on game day. Outside, the property unfolds as a private oasis, with a screened porch featuring Chicago brick pavers, a Wolf gas grill, Sub-Zero fridge, and refreshed finishes including a tiled backsplash, updated hardware, new sink and faucet, and refinished cabinetry. Chicago brick pavers also surround the free-form pool, creating a cohesive outdoor living environment. At the water’s edge, boaters will delight in the protected deep-water boat basin with two lifts (10,000-lb. and 16,000-lb. capacities), providing effortless maritime adventures. A detached oversized 3-car garage, connected by a covered walkway, provides ample space for storage or workshop use. Additional updates of note include updated HVAC systems, tankless water heaters, and modernized electrical throughout. A whole house generator rounds out the superlative systems. This exquisitely updated estate represents a rare offering where timeless elegance meets modern sophistication on one of Sarasota's most extraordinary waterfront settings.
Listing Agent: Kim Ogilvie (941-951-6660)
2327 HILLVIEW ST, SARASOTA, FL 34239
$2,100,000393 Days on yellowkey MLS ID: A4644963
Bed: 6 Bath: 6.5 Liv Area Sq Ft: 3500 Built: 2024Community: Battle & TurnerSingle Family
Remarks: Luxury Living Near Siesta Key and Downtown Sarasota! Experience the ultimate in luxury and comfort in this stunning 6-bedroom, 6.5 -bathroom coastal retreat. Designed for relaxation and effortless living, this home features a private heated pool, spacious outdoor living areas, and elegant interiors—perfect for those seeking a serene yet sophisticated lifestyle. Step into your own slice of paradise, where the heated pool invites you for a refreshing dip, and the expansive outdoor dining area and second-level balcony provide the perfect spaces to unwind. Whether you’re enjoying a morning coffee in the Florida sunshine or an evening cocktail poolside, this home offers an unparalleled outdoor experience. Inside, the open-concept layout creates a seamless flow between the living, dining, and kitchen areas. The chef’s kitchen is equipped with high-end appliances, ample counter space, and designer finishes, making it both beautiful and functional. With multiple spacious bedrooms, including four king suites and well-appointed bathrooms, comfort and privacy are at the forefront of this home’s design. Just a short drive from world-famous Siesta Key Beach, this home provides easy access to soft white sands, turquoise waters, and the vibrant Siesta Key Village. Enjoy boutique shopping, fine dining, and entertainment, all just minutes away. Don’t miss the opportunity to own this luxurious retreat—schedule your private tour today!
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Curt Ware (941-587-9122)
3451 FAIR OAKS PL, SARASOTA, FL 34239
$589,00035 Days on yellowkey MLS ID: A4685553
1 Days Off yellowkey (back on 3/25/2026)
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1515 Built: 1958Community: South GateSingle Family
Remarks: Under contract-accepting backup offers. South Gate Mid-Century Modern home with exceptional curb appeal! On an outstanding oversized corner lot and graced by a dynamic, majestic oak tree, this property immediately impresses. Go inside the open floor plan where your eyes are drawn straight through to the backyard, featuring a sparkling 49-foot saltwater lap pool with depths ranging from 3 feet to 10 feet, complete with new coping. The 1,524-square-foot paver pool deck, installed in 2024, provides ample space for relaxing and entertaining. The open kitchen features a center island, stainless steel appliances and stone countertops. Elegant plaster cove lighting surrounds the dining and living areas, adding warmth and character to the space. This home offers three bedrooms and 2.5 baths. The primary bedroom includes a cedar walk-in closet with custom shelving. Major updates and features include re-piped in October 2025 with Uponor PEX piping, deep well for irrigation installed in 2021 with pump added in 2022, roof replaced in 2019, water heater replaced in 2022, dried red cedar board fence installed in 2022, fully enclosing the yard with gates on both sides, hurricane protection throughout, including hurricane windows (2017) and clear panels (2017). The oversized garage (25 by 21.5 feet) includes a half bath, and a stackable washer and dryer replaced in 2018. The electrical subpanel was upgraded with an 80–100-amp feed, and the home is powered by PE Solar Enphase solar panels. Air conditioner is 2015 and maintenance done March 2026. The septic tank was replaced in 2007 and is being used for irrigation water retention. Add your personal finishing touches to make this incredible property your own. Ideally close to downtown Sarasota, you’ll enjoy easy access to dining, shopping, vibrant cultural attractions and the area’s beautiful Gulf Coast beaches. As photographed in the MLS, the wall-mounted TV, sound bar and stereo equipment will convey with the home.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Cindy Taliaferro (941-894-7269)
2360 LOMA LINDA ST, SARASOTA, FL 34239
$1,999,00025 Days on yellowkey MLS ID: A4687174
Bed: 4 Bath: 5.0 Liv Area Sq Ft: 3277 Built: 2027Community: Loma Linda ParkSingle Family
Remarks: One or more photo(s) has been virtually staged. Under Construction. Welcome to 2360 Loma Linda Street, a professionally designed new construction home in one of Sarasota’s most desirable locations. Spanning nearly 3,300 square feet with 4 bedrooms, 4 full bathrooms, and 2 half baths, the home combines clean architectural design with a layout that lives well, opening seamlessly to a private pool and outdoor space. Located just minutes from Downtown Sarasota, along with the area’s dining, shopping, and beaches, the setting offers both convenience and a strong sense of place. With construction in its early stages, buyers have the ability to be involved in selecting finishes and tailoring certain elements, creating a more personalized final product. At just over $600 per square foot, the pricing reflects strong value for new construction of this size and quality, especially from a builder known for delivering well-executed homes in this market. Inside, the entry foyer opens into a spacious great room that connects naturally to the kitchen and dining areas, all overlooking an oversized lanai and pool deck, creating an easy indoor-outdoor flow. The main level also includes a large walk-in pantry, laundry room, and powder bath, along with a first-floor primary suite featuring dual walk-in closets, double vanities with a makeup station, and a generously sized walk-in shower. Upstairs, there are three additional bedroom suites, each with walk-in closets and private en suite bathrooms, along with an additional powder room. A large bonus room completes the second level, offering flexible space for a media room, game room, or additional living area. Beyond its design, the home is being built with a focus on long-term durability, including placement outside of a flood zone, impact-rated windows and doors, and a metal roof designed for longevity, features that are becoming increasingly important for buyers in coastal markets. Overall, it’s a combination of design, location, and build quality that continues to stand out in today’s market. Reach out to learn more about the possibilities this beautiful Perkins & Powers Builders home has to offer.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Cole Collins (941-350-8360)
1739 CHEROKEE DR, SARASOTA, FL 34239
$4,499,000163 Days on yellowkey MLS ID: A4670822
0 Days Off yellowkey (back on 2/13/2026)
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 4538 Built: 2009Community: Cherokee ParkSingle Family
Remarks: Under contract-accepting backup offers. Nestled along Cherokee Drive in the prestigious Cherokee Park neighborhood, this residence enjoys a premier setting on one of Sarasota’s most sought-after streets, renowned for its graceful oak canopy and classic west-of-the-trail charm. This residence embodies the perfect balance of modern architecture, natural materials, and tranquil privacy. Designed by award-winning architect Guy Peterson and constructed by master builder Pat Ball, the home delivers a rare combination of architectural pedigree and enduring craftsmanship. Positioned on a gracious, estate-sized parcel surrounded by lush greenery, the home’s U-shaped floor plan wraps around its showpiece, a 45-foot crystal-clear pool with integrated spa, creating a seamless indoor–outdoor living experience that defines the Sarasota lifestyle. Outside, the stone pathway leading to the custom mahogany front door sets a striking geometric tone. Inside, board-on-board architectural molded concrete accent walls, Santos Mahogany wood floors, and cypress-accent ceilings strike a natural harmony with the home’s sleek, modern lines. Floor-to-ceiling impact-rated Marvin windows flood the interior with light, framing tranquil views of the pool and landscape from nearly every room. The wide-open living and dining area, anchored by a wood-burning fireplace, sets the tone for elegant yet effortless entertaining. The chef’s kitchen features Wolf and Sub-Zero appliances, extensive custom maple cabinetry, and a seamless connection to both indoor and outdoor dining spaces. In the west wing, the expansive primary suite serves as a private retreat with walls of glass overlooking the grounds, complemented by an adjacent executive office for work-from-home convenience. The east wing hosts two en-suite guest bedrooms, each with sliding glass doors opening directly to the pool. A detached guest cabana offers a complete living area, kitchenette, and en-suite bedroom that is ideal for visitors, extended stays, or use as a private art studio or executive home office. Located within Cherokee Park, one of Sarasota’s most established and beloved neighborhoods, this home offers walking distance to Southside Elementary, minutes to Southside Village and downtown Sarasota, and easy access to Siesta Key Beach, just five streets away. The community is known for its family-friendly gatherings, tree-lined streets, and timeless Sarasota character.
2323 OKOBEE DR, SARASOTA, FL 34239
$3,595,00025 Days on yellowkey MLS ID: A4687269
0 Days Off yellowkey (back on 3/23/2026)
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 3497 Built: 2026Community: Mcclellan ParkSingle Family
Remarks: Brand New West Indies inspired design located West of the Trail in McClellan Park. This stunning four-bedroom, four-and-a-half-bath residence offers exceptional design, thoughtful functionality, and spans close to 3500 square feet under air, complete with a den, bonus room, private elevator, and three-car garage. The primary suite is on the main floor along with the office and the other 3 bedroom suites and bonus room are upstairs. From the moment you arrive, the quality and attention to detail are unmistakable. Inside, the home features wide-plank French Oak flooring throughout both levels, solid-core doors, vaulted ceilings, and an abundance of custom built-ins. The chef’s kitchen is exceptionally appointed with matte finished custom cabinetry, professional-grade appliances, including a 48-inch GE Monogram dual-fuel range with six burners and griddle, Bosch dishwasher, wine refrigeration, and a large center island topped with quartzite, ideal for cooking, entertaining, and gathering. Outdoor living is equally impressive, featuring a saltwater pool and spa, outdoor kitchen, fire features, and a picture-window pool cage designed to maximize views while maintaining privacy. Lush, professionally designed landscaping surrounds the home, enhanced by low-voltage architectural uplighting in both the front and rear yards. Additional premium features include a locally sourced custom iron and glass front door, high-end bathroom finishes throughout, and a comprehensive AV and smart-home package with interior and exterior cameras, built-in speakers with SONOS technology, and multiple Frame TVs. This home also incorporates numerous energy-efficient and green features, including high-impact windows and doors, Icynene open-cell spray foam insulation, insulated garage doors, natural gas service, irrigation with well, and it comes Generator ready. The location is truly exceptional—West of the Trail, just minutes to the barrier islands and downtown Sarasota without the congestion, and only blocks from Southside Village, Sarasota Memorial Hospital, and top-rated Southside Elementary and Sarasota High School. This is a rare opportunity to own a brand-new, move-in-ready luxury home in one of Sarasota’s most desirable neighborhoods. If you like a home loaded with extras this home checks every box.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Ryan Carson (941-685-2879)
3319 S OSPREY AVE, SARASOTA, FL 34239
$1,995,00025 Days on yellowkey MLS ID: A4687005
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 3554 Built: 2023Community: Poinsettia Park 2Single Family
Remarks: A rare fusion of modern luxury, designer finishes, and an unbeatable Sarasota location, this stunning 2023-built residence at 3319 S Osprey Ave delivers the ultimate move-in-ready lifestyle just moments from Siesta Key Beach and Downtown Sarasota. Tucked within the highly sought-after Southside School District, this exceptional home by M&J Pham Development showcases impeccable craftsmanship, elevated design, and seamless indoor-outdoor living—perfectly tailored for those who appreciate both sophistication and comfort. From the moment you arrive, the home’s striking curb appeal, lush tropical landscaping, and expansive paver driveway set the tone for what awaits inside. Step through the front entry into a light-filled, open-concept floor plan where wide-plank luxury flooring, soaring ceilings, and a soft, coastal-modern palette create an airy and refined ambiance. The heart of the home is a show-stopping chef’s kitchen, thoughtfully designed with an oversized waterfall island, sleek custom cabinetry, quartz countertops, and a premium Fulgor Milano stainless steel appliance package, all illuminated by elegant designer lighting—creating the perfect space for both everyday living and elevated entertaining. The spacious living area flows effortlessly to the outdoor oasis through expansive glass doors, blending indoor and outdoor living with ease. Upstairs and throughout the home, generously sized bedrooms each feature private ensuite bathrooms and custom California Closets, offering both comfort and privacy for family and guests alike. The primary suite is a true retreat, boasting a spa-inspired bathroom with dual vanities, a soaking tub, a glass-enclosed walk-in shower, and a beautifully designed custom closet system. A versatile main-floor den provides the flexibility for a private office, formal dining space, or additional lounge, while the upstairs bonus loft with wet bar and wine refrigerator creates the perfect setting for entertaining, media nights, or hosting guests. Step outside to your private resort-style backyard, where a newly completed custom pool and spa (2024) takes center stage. Surrounded by lush tropical landscaping and expansive patio space, this outdoor retreat offers the perfect backdrop for relaxing in the sun, entertaining under the stars, or enjoying Sarasota’s year-round coastal climate. A covered lanai and second-story balcony further enhance the home’s outdoor living experience, providing multiple spaces to unwind and take in the serene surroundings. Additional highlights include a 2-car garage, dedicated laundry room, high-end finishes throughout, and meticulous attention to detail at every turn, making this home truly turnkey and move-in ready. Ideally located just minutes from Siesta Key’s world-renowned beaches, vibrant Downtown Sarasota, Sarasota Memorial Hospital, premier dining, shopping, and top-rated schools, this residence offers not just a home—but a lifestyle defined by luxury, convenience, and the very best of coastal Florida living.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Adnan Dedic (941-726-2917)
2363 MILFORD CIR, SARASOTA, FL 34239
$510,000318 Days on yellowkey MLS ID: A4654562
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1402 Built: 1960Community: Pittman-Campo SubSingle Family
Remarks: Step inside this lovingly updated Sarasota gem and experience the harmonious blend of classic Florida living and crisp, contemporary design. Nestled on a lush, professionally landscaped corner lot in a highly sought-after, no-HOA neighborhood, this 3 bedroom, 2.5 bathroom home delivers the open, sun-splashed lifestyle everyone is searching for. As you walk in, you will discover a true entertainer’s dream. The open-concept layout revolves around a beautifully designed chef’s kitchen outfitted with quartz countertops, a deep farmhouse sink, upgraded stainless steel appliances, and a striking stone-and-metal backsplash that sets the tone for unforgettable gatherings. The living and dining areas are flooded with natural light thanks to the home’s southern exposure and a series of sliding glass doors that line the walls, creating an effortless transition to the screened lanai and bringing the outdoors in. Bamboo flooring adds warmth and style throughout, complementing the fresh, coastal feel. The spacious primary suite is a private sanctuary featuring custom, hand-crafted solid-wood closet doors and a wide sliding glass door that opens directly to the lanai—a picturesque spot for enjoying a quiet morning coffee or a warm evening breeze. The second bedroom continues the theme of artisan touches with more custom closet doors, while the third bedroom, with its own separate exterior entrance and en-suite half bath, offers flexibility as a guest suite, home office, fitness studio, or creative space. The screened lanai is a true extension of the living area, featuring a beautifully crafted wood-accented ceiling that adds charm and character. This fully fenced outdoor space is ideal for relaxing, dining, or entertaining year-round. Encircling the home, vibrant tropical landscaping boosts curb appeal and creates a serene, secluded atmosphere—perfect for hosting casual neighborhood barbecues, unwinding with a good book in a hammock, or letting pets play freely. Located just a half mile from Arlington Park, this home serves as the prime gateway to a vibrant, active lifestyle with a wide array of local amenities right at your fingertips. From swimming laps at the aquatic center and working out at the gym to enjoying outdoor fitness stations, shooting hoops, playing tennis, or meandering along scenic walking trails, there’s no shortage of ways to stay engaged and connected. Even your four-legged friends will love the two nearby dog parks. Beyond the neighborhood, you’re only minutes from Sarasota’s world-famous beaches, its lively downtown arts and dining scene, and highly rated schools—all within one of the city’s most desirable and minimally restricted neighborhoods, and no HOA fees. Move-in ready and full of upgrades, NEW AC AND FENCE IN 2022. HOME WAS FULLY RE-PIPED IN 2023, GUTTER GUARDS AND FULL IRRIGATION SYSTEM. Don’t miss your chance, schedule your showing today and experience the lifestyle you've been dreaming of!
Listing Agent: Joey Lamielle (941-350-0016)
3085 GOLDENROD ST, SARASOTA, FL 34239
$459,000197 Days on yellowkey MLS ID: A4663967
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1608 Built: 1965Community: South GateSingle Family
Remarks: This rejuvenated residence sits on a ¼-acre in the heart of Southgate, a treasured community sought-after by families for its top-ranked school system. Locals appreciate the ideal proximity to downtown Sarasota’s arts and cultural venues, prized beaches, tons of recreational activities, and a wide variety of shopping and dining experiences. With 1,608 square feet of openness, this recently refreshed and upgraded home features 3 bedrooms and 3 baths. Casually comfortable interiors offer a pleasing neutral palette of beiges and creams that surround you in a quiet softness for easy Florida living. Natural light permeates this efficiently designed one-level home illuminating its modern conveniences and visual appeal. Adjacent to the living and dining area, the well-planned kitchen is highlighted by granite-topped island, hardwood cabinets, amazing backsplash, smooth surface cooktop, and stainless appliances including a side-by-side fridge, a built-in microwave and oven, a dishwasher, double sink and range hood. The baths feel luxurious with fully tiled walls matching the floors, vanities with granite countertops, and rich wood cabinetry. The three nicely-sized bedrooms are equipped with private baths and walk-in closets. Glass sliders open to a covered screen-enclosed porch that’s cozy and relaxing with a modern fire table adding a sparkle to cooler star-lit evenings. The fenced yard provides a large work shed, play area with swing set for the kiddos, ample area for barbecues with family and friends, or leisurely spot to kick back and enjoy life’s simpler moments. Everything throughout the home is new including ceiling fans, fixtures and finishes, solar panels for energy efficiency, high-volume water heater (2021), kitchen appliances (2019), ROOF, A/C, windows, PIPES LINED 2026 WITH A TRANSFERABLE WARRANTY, and tile flooring (2018). The newly-created ambiance of warmth and style has been done to perfection and will welcome you home with graciousness. Take the time to explore the many amenities at 3085 Goldenrod. Homes in this vicinity are in high demand and often sell quickly. Don’t miss this opportunity to make it yours. It might very well become your ideal place for years to come!
Listing is courtesy of: GRECO REAL ESTATE (941-685-0449)
Listing Agent: Karen Greco (941-504-6927)
1519 HARBOR DR, SARASOTA, FL 34239
$4,750,750149 Days on yellowkey MLS ID: A4672376
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 3970 Built: 2026Community: Harbor Acres Sec 2Single Family
Remarks: Under Construction. Harbor Acres, Sarasota's ultimate neighborhood in downtown living. The highly-acclaimed team of professionals at Allegra Homes has yet again created a vision of luxury, elegance and simplistic functionality. A dynamic 3,970 sq. ft. open layout is rich in gorgeous details everywhere you turn. Feast your eyes on the “St. Michael,” a two-story beauty with stunning curb appeal and exciting interiors thoughtfully designed for grand-scale living. The extended foyer and great room feature an amazing 21-ft ceiling and invite you into a fascinating space with see-thru views out to the magnificent outdoors. Step into the heart of the home, where the great room exudes warmth and sophistication. A wood-beamed ceiling adds character and warmth, while clerestory windows flood the space with natural light, creating an inviting and airy ambiance. Triple sliders seamlessly connect the indoors to the covered poolside lanai. In the family room, a stunning stone-faced center wall serves as the focal point, flanked by built-in shelving with elegant lighting. The consummate chef will delight in the variety of accoutrements offered in this delectable space honed to perfection. A large stone-topped island easily seats 5 and the premium appliance package encompasses a 36” Wolf induction cooktop, a 42” Sub-Zero fridge, a Wolf oven with matching drop-down microwave, an ASKO dishwasher, a Sub-Zero wine cooler, and adequate counter and storage space including a pantry. Adding stylish flair to the dining room is a builtin buffet with full mirrored wall and wide windows overlooking the tropical pool setting. A separate dry bar with pass-thru is convenient to both the great room and kitchen for ease of serving family and friends. Overlooking the pool is a bonus room with a pool bath and wall of pocketing sliders opening wide to a covered 545 sq. ft. outdoor oasis with tongue-and-groove ceiling, nicely equipped summer kitchen, and abundant room for both dining and lounging. The pavered lanai is enclosed with ClearView screening and includes a 25’x19’ heated pool with 6 stepping pads, spill over spa, sun shelf, LED bubbler, salt conversion generator and Pebble Tec finish. The owner’s wing, with an adjacent study, may become your most prized room of the home with its drop tray ceiling, spacious seating area, soaking tub inside an exquisite large glass shower, separate dual vanities and water closet. An additional bonus room with wet bar, two bedrooms and a bath are located upstairs. Other honorable mentions include a 3-car garage with epoxy floor, tankless gas water heater, 10-ft ceilings, modern staircase with floating steps, recessed lighting, crown molding, brick paver drive and walkway, 8’ interior solid core doors, professionally landscaped, and irrigation system. Poised on over a 1/3 acre lot in prestigious Harbor Acres with a sought-after central location near the arts, entertainment, dining, shopping, beaches, boating, golf and other year-round adventures. For families with elementary school-age children, top-ranked Southside School celebrates 120 years of excellence in academic achievement. This stately new residence has been masterfully crafted inside and out, and will add a sense of pride and joy to an already perfect lifestyle.
1509 FLOWER DR, SARASOTA, FL 34239
$5,375,000101 Days on yellowkey MLS ID: A4665815
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 4989 Built: 2026Community: Harbor Acres Sec 2Single Family
Remarks: Under Construction. Allegra Homes presents the custom-built Southside IV in Harbor Acres—one of Sarasota’s signature bayfront enclaves. Designed for elevated everyday living, this 5BR/4.5BA residence balances drama and comfort with a soaring great room, intricate millwork, and seamless indoor–outdoor flow to a covered lanai with summer kitchen and pool. An open chef’s kitchen with Wolf Professional appliances and stone countertops anchors the great room and dining area to create one cohesive gathering space. The main level offers a serene primary suite with expansive walk-in closets and a spa-style bath, a private guest suite, a dedicated office, and a bonus room that opens to the pool. Upstairs, three additional bedrooms are joined by a game room and loft for versatile living. Three-car garage on a large lot. Harbor Acres hugs Sarasota Bay just south of downtown—a long-established community known for convenience, comfort, and an elegant blend of classic and newer homes along beautifully landscaped, winding streets. Enjoy a short stroll to Southside Village (Morton’s Market, dining, and shops) and close proximity to Sarasota Memorial Hospital and Marie Selby Botanical Gardens; approximately 2 miles to downtown/bayfront and about 5.5 miles to St. Armands Circle, Lido Beach, and Siesta Key. Highly sought-after Southside Elementary School is roughly 1 mile away.
2343 PROSPECT ST, SARASOTA, FL 34239
$399,500203 Days on yellowkey MLS ID: A4666451
Bed: 3 Bath: 1.5 Liv Area Sq Ft: 1142 Built: 1954Community: Loma Linda ParkSingle Family
Remarks: 3 bedroom 1.5 baths and bonus room. Use it for a 4th Bedroom/Office or extra dining. Beautiful LVP flooring, stainless steel kitchen appliances and quartz counter tops. Large maintenance free back yard. Long carport and outside utility room with washer and dryer. Minutes from downtown, the Bay front and Hillview area.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Stephen Strong (941-201-9662)
2590 FLOYD ST, SARASOTA, FL 34239
$1,675,00079 Days on yellowkey MLS ID: A4680138
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2954 Built: 2025Community: Arlington ParkSingle Family
Remarks: Brand-new luxury home in Arlington Park, located in the highly desirable Rustic Lodge enclave. This 3 bedroom plus den, 3.5 bath residence offers exceptional design, high-end finishes, and a private outdoor oasis. Step into your private backyard retreat featuring a heated saltwater pool and a fully equipped outdoor kitchen with Blaze burner grill, granite countertops, and a Zephyr beverage center. Elegant pavers surround the entertaining area, while a grassy yard provides space for pets or gardening, perfect for indoor-outdoor Florida living. Inside, the foyer showcases porcelain tile flooring, flowing seamlessly throughout the home for a clean, modern look. A private office/den is conveniently located just off the entry. The open-concept living area centers around a show-stopping kitchen with custom Studio Luxe cabinetry extending to the ceiling, quartz countertops, a full-slab quartz backsplash, and a dramatic waterfall island. Thermador appliances include an induction cooktop, 42" built-in French door refrigerator, and combination wall oven. Upstairs, all bedrooms feature en-suite bathrooms and walk-in closets with custom shelving. And a luxurious primary suite with a spa-inspired bath. One-year builder warranty. Located just minutes from Downtown Sarasota, Siesta Key Beach, St. Armands Circle, Sarasota Memorial Hospital, the Legacy Trail, and top-rated schools. With no HOA and weekly rental eligibility within city limits, this home also presents an excellent vacation rental or investment opportunity.
Listing Agent: Laurie Minear (717-824-5703)
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