Location: Sarasota
Keyword(s): Sarasota High
Keyword(s) High School: Sarasota High
Do Not Show Listings
527 FREELING DR, SARASOTA, FL 34242
$5,825,000137 Days on yellowkey MLS ID: A4669657
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 4310 Built: 2026 Tax: $6,458 (2024)Community: Bay Island ShoresSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,458
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2024
Middle School: Brookside Middle
Remarks: Under Construction. The exterior presentation of this spectacular waterfront residence is most impressive with its blend of modern architecture and refined luxury. With superior elevation high above the water’s edge on Siesta Key’s prestigious Bay Island, this new to-be-built 4,310 sq. ft. residence is an unparalleled oasis of tranquility in a breathtaking setting. A place where architectural elegance and natural beauty converge in perfect harmony with elaborate artisanal work, functional design, and top-tier amenities. For boaters, the location is ideal with a new seawall and a private dock allowing quick access to the bay and gulf beyond. Built with intention and quality, large windows flood the space with natural light illuminating the graceful enhancements within. When entering the home through the 4-car garage, an elevator takes you to the first and second living levels. An elegant foyer entry with double-height ceiling and sleek iron-railed staircase usher you into the spacious interiors where every detail, from the fluid layout to the custom finishes, is thoughtfully curated. Adding a distinctive touch to the stunning great room are 20-foot ceilings and a two-story entertainment wall flanked by artistic display niches. A wall of glass sliders sets a dramatic tone, framing water views and uniting indoor-outdoor living. Designed for effortless entertaining and timeless family gatherings, the outdoor area overlooks the water to create a tranquil setting that feels both secluded and well-connected. With nearly 500 sq. ft. of covered lanai, an outdoor cook center and a heated pool/spa, there’s ample opportunity for hosting special gatherings or simply enjoying the quiet beauty laid before you. Lovely landscaping, lush greenery and outdoor spaces add to the home's overall aesthetic appeal. A remarkable gourmet kitchen is designed for functionality and style, equipped with high-end finishes, top-tier appliances, a large island and a butler’s pantry with additional refrigerator and dishwasher. An adjoining dining room comfortably seats 8-10 and offers wonderful water views while dining. The primary wing is remarkable with an exquisite spa bath, enlarged customized wardrobe room, and direct access to the laundry facilities. The first level also includes a den suite ideal for remote work or creative pursuits and a completely private guest bedroom with its own full bath. Upstairs, there’s an overlook to the great room below, 2 bedrooms, 2 full baths, and an amazingly-sized bonus room with private balcony. The award-winning and talented team of professionals at Allegra Homes has thoughtfully and expertly created a residence offering a secure, exclusive lifestyle in one of Sarasota's most sought-after and high-value areas. The construction quality is of the highest standard, ensuring that the home is both beautiful and built to last. Just minutes to the mainland, downtown’s cultural mecca, world-class dining and shopping venues, gorgeous area beaches and a top-ranked school system coveted by families for generations, the prized waterfront location couldn’t be better. Showcasing extraordinary craftsmanship throughout, this never-lived-in showplace is the ultimate vision for those who value the very best of coastal Florida living. There’s still time to make your own personal choices for creating the perfect custom home tailored to your family’s taste and style.
Listing is courtesy of: GRECO REAL ESTATE (941-685-0449)
Listing Agent: Karen Greco (941-504-6927)
1260 DOLPHIN BAY WAY #404, SARASOTA, FL 34242
$1,395,000150 Days on yellowkey MLS ID: A4673762
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2200 Built: 1997 Tax: $12,793 (2025)Community: Dolphin BaySpa: YesCondo
Taxes:$12,793
Tax Year: 2025
Remarks: ENJOY SERENE INTRA-COASTAL WATER VIEWS from this this 4th floor, end unit, 3 bedroom, 3 full bath condo at Dolphin Bay. This community lives life to the fullest! Lots of social activities and friendly and caring neighborhood. Take a new look and enjoy the fresh new decor and new high impact windows and sliders, all added in 2025! Reduced condo fees. This meticulously maintained condo lives like a single family home with charm and character. The kitchen was custom built by Yoder Construction, a well-known local company, highly respected for their craftsmanship. Living room and dining area are bright and spacious. The large primary bedroom has a walk-in closet and ensuite with shower and separate soaking tub. There are two other ensuite bedrooms. All three bedrooms have California Closet systems. All windows have custom plantation shutters, adding to the charm and comfort of this amazing condo. You will want to spend your day on the light filled lanai, perfect for entertaining or simply relaxing. Dolphin Bay is a highly desirable, gated, pet friendly, 50-unit complex with a fun filled community atmosphere with three Har-Tru tennis courts, an active clubhouse, fitness center, pool and spa, day dock, fishing pier and kayak access. Dolphin Bay is well maintained with a freshly updated exterior and new elevators in 2024 and beautifully landscaped grounds. Just a short walk to the world famous, white crystal sands of Siesta Key beach.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Mina Johnson (941-404-9347)
1939 HIGH POINT DR, SARASOTA, FL 34236
$1,335,000116 Days on yellowkey MLS ID: A4676860
REDUCED by $20,000 (1.5%) on 04/15/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2478 Built: 1954 Tax: $8,592 (2025)Community: High Point CircleSingle Family
Taxes:$8,592
Elementary School: Southside Elementary
Middle School: Sarasota Middle
Remarks: Tucked just moments from Hudson Bayou and Sarasota Bay, this gated mid-century modern compound offers a rare opportunity to own a meaningful piece of Sarasota’s architectural and artistic history while embracing a lifestyle that feels both inspired and entirely livable. Originally built in 1954 as a Ruth Richmond design and later reimagined by nationally recognized abstract artist Steve McCallum, the property blends authentic mid-century lines with bold creative character. Set behind walls and framed by lush tropical landscaping, the home unfolds as a private retreat within one of Sarasota’s most desirable cultural corridors. A paver drive leads to the striking architectural façade, clerestory windows, and modern courtyard entry. Inside, natural light pours through high transom windows and expansive sliding glass doors, highlighting the openness and warmth that define true mid-century design. The main residence offers three bedrooms and two full baths, with an open living and dining layout that flows effortlessly to the courtyard pool. Clean lines, tile flooring throughout, and thoughtful updates create a space that feels timeless yet comfortable. The private courtyard pool anchors the compound, surrounded by palms, bamboo, and multiple seating areas designed for relaxed evenings or intimate gatherings. The setting offers privacy without sacrificing proximity to downtown and the bayfront. The studio structure truly elevates the estate. Measuring approximately 56 by 32 feet with soaring 16-foot ceilings, it was purpose-built for large-scale creative work and now offers remarkable flexibility. With its own private entrance and a dedicated bathroom, the studio can function independently as a guest retreat, executive workspace, gallery-style studio, or wellness space. The space also includes a walk-in closet area that currently functions as both a walk-in closet and laundry room, adding additional convenience and functionality. An interior hallway also connects it to the main home, allowing seamless use for multigenerational living or extended guests while maintaining the option for complete privacy. For several years, the studio operated as a curated, owner-hosted guest experience, earning more than 200 five-star reviews and establishing itself among Sarasota’s earliest luxury short-term stays. That history speaks to its design appeal, comfort, and versatility. In addition to the main living spaces, the property also features an approximately 200 square foot storage room connected to the studio. This flexible area can easily function as an extension of the studio when the roll-up door is opened, creating additional usable space for creative work, storage, or studio expansion. Offering 2,478 square feet under air across both structures, this property delivers architectural authenticity, creative scale, and compound-style living just minutes from downtown dining, galleries, and Sarasota’s renowned arts scene. This is a mid-century modern lifestyle property for those who value design, flexibility, and the freedom to shape a home around how they truly want to live. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Toni Zarghami (941-248-2147)
1714 SOUTH DR, SARASOTA, FL 34239
$2,245,00042 Days on yellowkey MLS ID: A4686448
Bed: 4 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 3105 Built: 1950 Tax: $11,204 (2025)Community: Cherokee ParkSpa: NoSingle Family
Taxes:$11,204
Remarks: One or more photo(s) has been virtually staged. Tucked beneath a canopy of mature trees in one of Sarasota’s most coveted neighborhoods, 1714 South Drive presents a rare opportunity to secure a prime homesite in Cherokee Park, West of the Trail and moments from the very best of Sarasota living. Set on a beautifully established lot with lush, mature landscaping, a paver driveway, and a combination of garage and carport parking, the property offers an immediate sense of privacy and presence. Inside, the home unfolds with a surprisingly expansive footprint and a floor plan that captures natural light throughout. A welcoming entry with a leaded stained-glass door opens to multiple living spaces, including a living room with a wood-burning fireplace, custom built-ins, and distinctive Saltillo tile flooring, alongside a light-filled family room wrapped in windows with views of the pool and direct access to the lanai. The dining room, positioned with a bay window overlooking the pool, connects seamlessly to the kitchen, which features granite countertops, glass-front cabinetry, a center island with cooktop, and a breakfast nook with access to a private side deck. The layout offers flexibility with multiple bedroom and office options, including a front bedroom or office with a wall of windows and an in-wall safe, and a private guest suite with its own bath showcasing vintage turquoise tile and retro detailing. A secondary guest bedroom includes built-in workspaces and shelving, ideal for dual office use or creative space. The primary suite is tucked privately toward the rear of the home, offering direct access to the lanai, abundant natural light, and a spacious bath with dual vanities, soaking tub, walk-in shower, and skylight above. Additional spaces include a bonus room off the garage with bedroom conversion potential, a pool bath, and a separate flex space off the lanai with wood-paneled walls and its own mini-split system, ideal for a studio, gym, or additional lounge. Outdoors, the home continues to deliver with an oversized, caged pool and covered lounging areas, surrounded by mature landscaping, stone walkways, and a fully fenced yard. An existing outdoor kitchen structure and multiple access points from the home create a true indoor-outdoor flow that aligns perfectly with Sarasota’s year-round lifestyle. What truly elevates this property is its location. Just moments from the shops and restaurants of Southside Village or downtown Sarasota’s waterfront, cultural venues, and marina. It is close to Sarasota Bay and just a short drive to Siesta Key’s north bridge. This is a setting that defines convenience and coastal luxury. Cherokee Park remains one of the most desirable addresses in Sarasota, and 1714 South Drive offers the rare combination of location, lot, and layout, an exceptional opportunity in the heart of Sarasota.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
1389 TANGIER WAY, SARASOTA, FL 34239
$5,985,000105 Days on yellowkey MLS ID: A4677509
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 5310 Built: 2003 Tax: $39,106 (2025)Community: San Remo EstatesSpa: YesSingle Family
Taxes:$39,106
Remarks: One or more photo(s) has been virtually staged. Step into a private, gated waterfront estate in Sarasota offering deep-water boating access, refined coastal architecture, and an unsurpassed location just minutes to Siesta Key Beach, Southside Village, and downtown Sarasota. Located in the coveted San Remo Estates community, this exceptional residence blends timeless elegance with modern functionality—perfect for buyers searching for a luxury Sarasota waterfront home with privacy and proximity to the city’s best dining, shopping, and beaches. Designed by renowned architect Walter Hamm and built by Bill McGinness, the home is engineered for lasting stability with construction supported by 54 concrete pilings, a powerful value point for buyers seeking a well-built coastal property. Set on a sprawling private lot with mature landscaping and serene surroundings, the home captures panoramic water views and features a protected deep-water harbor, ideal for boaters who want quick access to Sarasota Bay and Gulf. Inside, the home showcases a bright, open layout filled with natural light, elevated by custom millwork, coffered ceilings, rich wood flooring, and polished travertine. The gourmet kitchen is designed for both entertaining and everyday living, featuring an oversized center island, quartz countertops, premium wood cabinetry, granite perimeter counters, subway tile backsplash, and stainless-steel appliances, along with an inviting breakfast nook that overlooks the water. The adjacent family room creates a warm gathering space, while the formal dining room is ideal for hosting. A private office provides a quiet, dedicated workspace, ideal for today’s lifestyle. The primary suite on the main level is a true waterfront retreat with oversized windows framing tranquil views, two custom walk-in closets, and a spa-style bath with a floating vanity, illuminated mirrors, a freestanding soaking tub, and an oversized walk-in shower. Upstairs, the second level is designed for comfort and entertaining with three generous bedroom suites, a TV/game room, a convenient kitchenette, and a terrace that overlooks the pool and peaceful waterscape, perfect for guests, multi-generational living, or extended stays. Outdoor living is equally impressive, featuring an expansive travertine pool deck, a heated pool and spa, a fenced and spacious yard, and lush tropical landscaping that creates a resort-style environment with exceptional privacy. Andersen sliding doors and windows enhance the indoor-outdoor connection and raise the overall quality of the home. A comprehensive renovation completed in 2015 elevated the interiors with sophisticated, updated finishes, while key improvements include a new roof (2020) and updated AC systems (2023 & 2024). Additional features include an ADT security system, generous storage, abundant closet space, a large laundry room, provisions for an elevator, and an oversized three-car garage. Sought-after San Remo Estates is positioned at the heart of Sarasota, just before the north bridge to Siesta Key, making it one of the most desirable locations for those wanting a Sarasota luxury waterfront home with both convenience and privacy. This exceptional coastal estate delivers the ultimate Florida lifestyle: deep-water boating, serene water views, and effortless access to Sarasota’s beaches, culture, and world-class amenities.
33 S PALM AVE #1503, SARASOTA, FL 34236
$1,495,000148 Days on yellowkey MLS ID: A4674241
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1122 Built: 2024 Tax: $14,396 (2025)Community: DemarcayCondo
Taxes:$14,396
Middle School: Booker Middle
Remarks: Discover the elegance of living in your very own private and luxurious residence, at one of Sarasota’s newest and premier condominiums, the DeMarcay. Experience the vibrance of residing in the heart of Sarasota where you can explore; art galleries, first rate theaters, the opera, a library, diverse dining, service options, shops including Whole Foods, and a beloved Saturday market. Within a block of Sarasota’s famous bayfront, boasts boat charters, rentals, and tours, as well as Marina Jack’s, a local mainstay with boat and yacht dockage, has an indoor piano bar and patio area for catching the sunset, happy hour, casual dining, or venturing upstairs for fine dining. For a more laid back, casual choice and one of Sarasota’s favorite old Florida spots, O’Leary’s Tiki Bar. Once you enter the DeMarcay by using the modern Butterfly entry system, a concierge and valet staff are available to take care of the owner's garage parking and other needs. Taking the elevator up to your beautiful 2-bedroom, 2 bath condominium on the 15th floor with magnificent city and Sarasota Bay water views, you will be surrounded by multiple high-end upgrades. A beautiful open kitchen with quartz countertops and waterfall kitchen island overlooks the dining and living room and outside patio. An exquisitely custom-built wall center and dry bar that includes wine refrigeration is one that any connoisseur of fine wines and liquors would appreciate. This unit also boasts ceramic and porcelain tiles, custom modern lighting fixtures throughout, and a master en-suite with custom walk-in closet. With property amenities second to none, your new home has options of storage, use of a full gym, and an exquisite clubhouse that includes a large entertaining are and an outdoor pool and kitchen for year around entertaining.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Coreen Wilde (941-960-5557)
1705 WISCONSIN LN, SARASOTA, FL 34239
$3,950,00019 Days on yellowkey MLS ID: A4689693
1 Days Off yellowkey (back on 4/15/2026)
Bed: 5 Bath: 6.0 Gar: 5 Liv Area Sq Ft: 4871 Built: 2016 Tax: $39,893 (2025)Community: Acreage & UnrecSpa: YesSingle Family
Taxes:$39,893
Remarks: Under contract-accepting backup offers. Tucked behind a gate on a quiet, private road in one of Sarasota’s most sought-after neighborhoods, this is the kind of property families wait years for—where space, privacy, and lifestyle all come together just minutes from everything. Located West of Trail, just blocks from Southside Elementary and Southside Village, and a short drive to downtown Sarasota and Siesta Key Beach, this estate offers a rare balance: a secure, expansive family compound in the heart of it all. Set on over half an acre and fully gated, fenced, and lushly landscaped, the property is designed for those who want room to live, grow, and entertain privately—without sacrificing convenience. The main residence spans nearly 4,000 square feet with 5 bedrooms, 4 full bathrooms, 2 half baths, a private office, and a large game room or playroom with its own wet bar—perfect for families who need flexibility in how they live day-to-day. Whether it’s a dedicated workspace, kids’ zone, or media room, the layout adapts to your lifestyle. The kitchen is built for real life and entertaining alike, featuring Viking appliances, generous storage, and an open flow into the main living areas and outdoor spaces. Every bedroom includes an ensuite bath, offering comfort and privacy for family and guests. Step outside and the home truly opens up. A large covered lanai with outdoor kitchen overlooks the heated, self-sanitizing saltwater pool and spa, with a sunken firepit seating area creating a natural gathering space for evenings with friends or family. A dedicated pool bath adds convenience, while the entire outdoor experience is designed for year-round Florida living. For those who need more than just bedrooms, the detached guest apartment above the garage provides over 700 square feet of private living space—ideal for multi-generational living, a nanny suite, long-term guests, a studio, or a secluded home office. And for the car enthusiast or collector, this property stands apart. With 5+ climate-controlled garage spaces—including room for lifts—plus a large all-season carport with motorized louvers, you have the flexibility to showcase, protect, and enjoy your collection. The garages are outfitted with SwissTrax flooring, vacuum systems, and Mitsubishi in-wall AC units—built with intention, not as an afterthought. Beyond comfort and design, the home is equipped for peace of mind. Impact windows and doors, a full CCTV security system, smart home integration, and a Generac generator ensure both safety and ease of living. This is a home for a family who wants it all—space to spread out, privacy to feel secure, proximity to top schools and amenities, and the ability to live an active Sarasota lifestyle, whether that’s golf cart rides to dinner, beach days on Siesta Key, or quiet evenings at home. Because homes that check every box like this—location, land, layout, and lifestyle—are rare. And when they come up, they don’t last.
Listing is courtesy of: EXP REALTY LLC (800-486-1794)
Listing Agent: Mark Coppens (941-444-0436)
3314 CHARLES MACDONALD DR, SARASOTA, FL 34240
$1,850,00084 Days on yellowkey MLS ID: A4681339
REDUCED by $100,000 (5.1%) on 04/04/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3221 Built: 1999Monthly Fee: $369 Tax: $8,486 (2025)Community: Laurel Oak Estates Sec 01Spa: YesSingle Family
Taxes:$8,486
Elementary School: Tatum Ridge Elementary
Middle School: McIntosh Middle
Remarks: Under contract-accepting backup offers. Welcome to this exceptional custom Arthur Rutenberg residence, thoughtfully updated with luxurious finishes throughout. This rare offering blends timeless architectural design, quality craftsmanship, privacy, and breathtaking golf course views—creating a serene setting for elevated Florida living. Perfectly positioned along the 8th hole of the Jones Golf Course, the home offers a tranquil backdrop for everyday living and entertaining. A dramatic arrival begins with a complete landscape redesign, professional lighting for privacy and evening ambiance, a pavered driveway and walkways, and modernized entry pillars. Enter through grand African mahogany doors into a striking interior featuring rich luxury wood flooring, wood beam accents, and an open flowing floor plan. A dramatic stone accent wall and custom niches define the main hallway, while redesigned living spaces throughout offer both elegance and versatility. The formal dining room showcases a dedicated wine cellar accented by a distinctive antique door. The game room provides flexibility and can also serve as a formal living room. The chef’s kitchen is the heart of the home, featuring custom Magnolia cabinetry with quartz counters, a striking custom copper hood, an oversized six-burner gas range with double ovens and griddle, and two expansive islands with both main and prep sinks. High-end built-in appliances complete this incredible kitchen and include an integrated refrigerator, refrigerator drawers, warming drawer, two Bosch dishwashers, and an under-counter microwave drawer. The adjacent living area features a custom wood entertainment wall designed to accommodate a large television—ideal for hosting gatherings. The spacious primary suite offers a peaceful retreat with his-and-hers walk-in closets and a generously sized bath with dual vanities ready for personal customization. Two additional guest bedrooms are equally well-appointed plus a 4th bedroom currently being used as a den providing ideal living for family or guests. All guest bathrooms plus powder room have been completely updated with designer tile and custom vanities. Step outside to the stunning outdoor living area, where the pool and lanai were completely remodeled in 2023. Updated pool/lanai highlights include marble decking, a sun shelf, pool water features, a clear-view pool cage enclosure and a saltwater pool system including new equipment/gas heater. A decorative tile accent wall and wood-paneled ceiling complete this outdoor private oasis, offering unmatched tranquility with panoramic golf course views. Additional upgrades of this stunning home include hurricane-impact windows (2022), plantation shutters throughout, a new slate tile roof (2022), new AC (2024), hot water heater (2025), interior and exterior paint (2025), and a whole-house Kinetico water treatment system. Residents of Laurel Oak Estates enjoy the option to join the Laurel Oak Country Club, featuring two 18-hole championship golf courses, 12 Har-Tru tennis courts, six pickleball courts, a junior Olympic-size heated pool, a beautifully updated clubhouse, and an active social calendar. Reciprocal privileges with Bird Key Yacht Club, along with close proximity to I-75, downtown Sarasota, UTC Mall, medical facilities, dining, entertainment, and world-famous Siesta Key Beach, complete this lifestyle. This is resort-style living at its finest—offering privacy, serenity, and an unparalleled setting within one of Sarasota’s premier gated communities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Lori Lockhart, Pa (941-724-0595)
3281 BENEVA RD #104, SARASOTA, FL 34232
$209,95017 Days on yellowkey MLS ID: A4690039
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 964 Built: 1979 Tax: $874 (2025)Community: Village Brooke Sec 3Condo
Taxes:$874
Elementary School: Wilkinson Elementary
Remarks: Nicely appointed and recently updated condominium awaits those looking for the Florida Lifestyle in an adorable package. Village Brooke is located minutes to gulf beaches, downtown, restaurants, shops...very convenient. The community itself features an active clubhouse, multiple pools for easy walking access from any home, tennis courts and a park like setting. Notice the monthly fees...very reasonable to include building insurance, water and sewer in addition to the onsite manager. This corner first floor unit has been occupied by the current owner since 2010...never rented and it shows! Warm color ceramic tile and waterproof luxury vinyl plank, new granite, custom shaker cabinets, upgraded appliances and so much more. The bathrooms have been updated as well...and last not least...a brand new permitted eletrical panel for that insurance discount and peace of mind. Call today for a private tour.
Listing is courtesy of: SARASOTA REAL ESTATE LIVE (941-232-5672)
Listing Agent: Cor Donovan (941-232-5672)
546 FREELING DR, SARASOTA, FL 34242
$12,500,00017 Days on yellowkey MLS ID: A4687147
Bed: 5 Bath: 6.0 Gar: 10 Liv Area Sq Ft: 4353 Built: 2027 Tax: $17,536 (2025)Community: Bay IslandSpa: YesSingle Family
Taxes:$17,536
Remarks: Pre-Construction. To be built. Discover an extraordinary opportunity to own an expansive double lot of 0.52 acres on North Siesta Key with this single-story, new construction transitional modern-style luxury home by Pham Development. Offering 170 feet of deep-water canal frontage, the residence features 4,353 square feet under air and 15,453 square feet under roof. With 5 bedrooms, 5 full bathrooms, 2 half baths, and a designated private office, the home showcases soaring 17.5-foot vaulted ceilings and a striking glass wine wall, complemented by designer finishes that fill the interiors with natural light and tranquil water views. Across the canal, lush landscaping provides a serene and private backdrop, with flexibility to customize finishes and style. Designed for both comfort and entertaining, the open-concept living spaces flow seamlessly to a resort-style outdoor retreat. The expansive back patio is equipped with remote-controlled electric mosquito screens, allowing you to enclose the space at the touch of a button for year-round enjoyment. Enjoy a spectacular pool with a champagne hot tub spa, a generous patio, and a fully equipped outdoor kitchen perfect for alfresco dining. A scenic path leads to your private dock with a state-of-the-art electric system and space for a boat up to 37 feet, offering smooth access to the bay and Gulf. The primary suite is a private sanctuary with spa-inspired amenities and dedicated quarters. A chef’s kitchen anchors the heart of the home with premium appliances and refined finishes. An elegant circular driveway creates a grand entrance, while the expansive ground level offers room for up to 10 cars, complemented by an impressive 10-car garage—ideal for collectors or additional storage. This exceptional waterfront residence delivers effortless luxury and refined coastal living.
Listing is courtesy of: PHAM REALTY GROUP LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
4650 10TH ST, SARASOTA, FL 34232
$1,875,00017 Days on yellowkey MLS ID: A4689601
Bed: 5 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 2915 Built: 2017 Tax: $11,533 (2025)Community: Acreage & UnrecSpa: NoSingle Family
Taxes:$11,533
Elementary School: Brentwood Elementary
Remarks: Welcome to your dream oasis in the heart of Sarasota, close to I-75 just North of Fruitville. This stunning, newer build boasts a prime location that perfectly couples lifestyle with tranquility. Situated on just under 1 acre, this coastal contemporary offers the perfect blend of modern luxury and serene natural beauty. As you drive onto the property, you'll be greeted by a private setting that instantly puts you at ease; providing a retreat-like atmosphere that's hard to find West of I-75.The main residence showcases simplistic yet thoughtful design, with every detail carefully curated to create an atmosphere of elegance and comfort. The open layout with polished concrete floors allow for seamless flow between living spaces, making it ideal for both entertaining and everyday living. At the heart of the home is the beautifully appointed kitchen, featuring top-of-the-line Thermador appliances that cater to the needs of any chef or baker. The fine craftsman styling with transom windows and custom millwork are a real treat. As you step out to your lanai, you'll discover a private outdoor haven that invites relaxation and leisure. Lounge on your spacious patio, complete with outdoor kitchen perfect for al fresco dining or simply enjoying the Florida sunshine in the gorgeous pool. With a nod to versatility, this property also includes a secondary building that offers endless opportunity. Compete with a rare and highly desirable upstairs guest apartment boasting 266 sqft of space. This brand new, never lived in studio, comes complete with a full bath and washer/dryer. Whether you envision a home office, a personal gym, or an art studio this space can adapt to your desires with ease. The 28’ x 48’ garage is large enough to house your offshore boat, RV, car collection or equipment. Don't miss the chance to own this exceptional property, where newer construction, prime location, and coastal contemporary design come together in perfect harmony. Experience the best of Sarasota living in your own private sanctuary. Schedule your private showing!
Listing Agent: Jeff Hinrichs (941-456-1251)
1740 S ORANGE AVE, SARASOTA, FL 34239
$1,500,00095 Days on yellowkey MLS ID: A4679755
REDUCED by $100,000 (6.3%) on 04/15/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3168 Built: 1967 Tax: $11,676 (2025)Community: Harbor Acres Sec 2Single Family
Taxes:$11,676
Remarks: One or more photo(s) has been virtually staged. Discover the ultimate Sarasota lifestyle in this charming home situated in one of the city's most coveted neighborhoods. This property offers the rare luxury of true walkability; stroll to Southside Village for your morning coffee, pick up fresh ingredients at Morton’s Gourmet Market, or enjoy dinner at a handful of top-rated local restaurants just steps from your door. For those who love the city energy, downtown Sarasota is just a short walk or bike ride away. Enjoy the peace of mind that comes with a home where the major work is already complete. A comprehensive plumbing update replaced both supply and drain lines throughout the majority of the home in 2020/2021. The property feels brand new, featuring fresh exterior paint (2026) and pristine flooring installed in the bedrooms in 2024 and the main living areas in 2026. This residence is also perfectly suited for multi-generational living; the flexible floor plan offers the ideal opportunity to convert a portion of the home into a private in-law suite. Outside, you will find a massive, wide-open backyard that is a true private oasis. The expansive green space is perfect for family activities, entertaining, or future expansion. It features a variety of lush plants and mature trees, all kept vibrant by a custom irrigation system installed in 2021. Don’t miss this opportunity to own a move-in ready home in the heart of it all.
Listing Agent: Jose Hugo Martinez (941-373-5570)
2529 GOLDEN POINCIANA PL, SARASOTA, FL 34232
$324,90026 Days on yellowkey MLS ID: A4688911
1 Days Off yellowkey (back on 4/14/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1302 Built: 1977 Tax: $3,199 (2025)Community: Brentwood EstatesSingle Family
Taxes:$3,199
Remarks: Under contract-accepting backup offers. 3D VIRTUAL TOUR AVAILABLE: CLICK ON VIRTUAL TOUR LINK #1. Very nice 3 bedroom, 2 bath home with a spacious yard and room to park an RV on the side of the home (or a trailer, box truck, boat, etc). This home has a roof from June 2022, and a wonderful back yard with plenty of eureka palms, providing a lush garden feel and additional privacy from the neighbors. Welcome to this charming single-story home offering a blend of comfort, functionality, and opportunity. Featuring a durable shingle roof and a spacious driveway with a one-car garage, this property sits on a generously sized lot with mature trees that provide shade and privacy. Inside, you’ll find an open-concept living and dining area with tile flooring throughout, making for easy maintenance and a clean, cohesive look. The kitchen offers ample cabinet space, formica countertops, and a practical layout that flows seamlessly into the main living areas—ideal for everyday living and entertaining. The home includes three bedrooms with ceiling fans, good natural light, and closet storage. The bathrooms have been updated with modern vanities, fixtures, and a walk-in shower design for a fresh, functional feel. Additional highlights include: Spacious laundry/utility area with extra storage, Attached garage with shelving and workspace potential, Large backyard with room for outdoor living, gardening, or future improvements. This property presents a great opportunity for buyers looking to personalize a home or invest in a well-located property with solid fundamentals. Conveniently situated near local amenities, shopping, dining, and major roadways. Don’t miss the chance to make this versatile property your own—schedule your showing today!
Listing is courtesy of: FATHOM REALTY FL LLC (888-455-6040)
Listing Agent: Maciek Zaremba (941-400-7084)
105 ISLAND CIR, SARASOTA, FL 34242
$2,680,950379 Days on yellowkey MLS ID: A4647817
0 Days Off yellowkey (back on 4/14/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2750 Built: 1953 Tax: $7,593 (2024)Community: Palm IslandSpa: YesSingle Family
Taxes:$7,593
Remarks: Under contract-accepting backup offers. Pre-Construction. To be built. Pre-Construction. To be built. IMAGINE a Custom Coastal Contemporary Home on Palm Island, Siesta Key. Picture a thoughtfully designed residence offering 2,750 sf of indoor living space and 3,467 sf of total indoor/outdoor space. E/M Custom Homes is renowned for their impeccable craftsmanship and modern coastal design creating a one-of-a-kind residence to be tailored to your lifestyle. This stunning 4-bedroom, 3.5-bath home includes an open Concept Floor Plan, Gourmet Kitchen with custom cabinetry, luxury appliances, and a walk-in pantry—ideal for entertaining. Enjoy a First-Floor Master Suite with a spa-inspired en suite bath and a large walk-in closet. The Second Floor boasts 3 bedrooms, a second gathering room, an office, a laundry room, and a Balcony to relax and enjoy island breezes and views. Be inspired to grill in your Outdoor Kitchen on the expansive covered lanai, perfect for alfresco dining. Lounge in your Custom Designed Private Pool, appreciating outdoor living. You also have an Oversized 2-Car Garage with easy access to the downstairs Laundry/Mudroom entry. Set on 2 lots, totaling 0.45 acres (19,456 sf), this property offers a rare combination of space and luxury. Just a 2 block stroll to sink your toes into the luxurious quartz sand and sparkling water of our award-winning Siesta Key Beach. The Village is minutes away where you will find fabulous restaurants, live music, specialty shops, night life, Sunday Farmers Market, art festivals and more. Your dream coastal lifestyle awaits!
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Linda Scheller, Llc (941-806-7981)
1275 SIESTA BAYSIDE DR #1275, SARASOTA, FL 34242
$999,00052 Days on yellowkey MLS ID: A4684885
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1645 Built: 1988 Tax: $9,421 (2024)Community: Gulf & Bay Club BaysideCondo
Taxes:$9,421
Remarks: An amazing year-round residence, vacation or investment property! Don't miss this rare opportunity to own a beautifully furnished 3-bedroom, 2-bath + loft unit just steps from world-renowned Siesta Beach with dedicated beach access. Recently renovated, this turnkey residence features a bright open floor plan with wood-look tile, shiplap accents, and raised ceilings in the hallways, kitchen and dining areas, a rare update in the community. The kitchen boasts full height solid wood cabinetry, quartz countertops, stainless appliances, and a charming, windowed breakfast nook. Enjoy multiple dining options including a formal area, bar, and a glass-enclosed lanai, perfect for entertaining. The spacious primary suite opens to a Florida room with tongue and groove wood ceiling overlooking a serene pond and wildlife, with a renovated ensuite featuring dual sinks, walk-in shower, abundant storage, and a large closet. Upstairs includes a versatile loft, two guest bedrooms, and a full bath. Relax on the inviting front porch with views of Siesta’s iconic sunrises and sunsets. Additional perks include a one-car garage, private driveway, and in-unit laundry. Unit has all brand new screens. Located in Gulf & Bay Club Bayside, a gated community with resort-style amenities: two pools, tennis/pickleball courts, clubhouse, fitness center, sauna, fishing pier, walking paths, and BBQ areas. On-site management and a one-week rental minimum make this a standout investment property with income potential of $80k plus. Spend your days enjoying effortless beach access for sunrise coffee, long shoreline walks, and unforgettable Gulf sunsets. When it’s time to explore, Siesta Key Village is just minutes away with favorite restaurants, local shops, and live music—an unbeatable setting to experience Siesta Key at its finest.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Robert Ruiz (941-544-3299)
3135 ALTA VISTA ST, SARASOTA, FL 34237
$419,900233 Days on yellowkey MLS ID: A4664729
2 Days Off yellowkey (back on 3/11/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1502 Built: 1956 Tax: $310 (2025)Community: Bellevue TerraceSingle Family
Taxes:$310
Elementary School: Alta Vista Elementary
Remarks: LOCATION! LOCATION! Bellevue Terrace! Fantastic opportunity to purchase this beautifully renovated 3 bedroom 3 bathroom home on a very spacious lot. This is an open, split level home with large fenced-in back yard, with room for a pool. The first floor has a large living room/dining room combo, kitchen and half bath. It includes bran new large floor tiles, new hard wood cabinets with quartz tops. All new appliances. The top level has 3 bedrooms with original hardwood floors and 2 full renovated bathrooms. The lower level has a large bonus room that lets lots of light in, and separate laundry room with new washer and dryer leading to the garage. Additional renovations include new shingle roof, electric panel and hot water heater. PVC water lines. The property also has side parking for an RV or Boat. This home is just minutes to downtown Sarasota and a very close proximity to the Lido Beach, Legacy Trail, Payne Park, Sarasota High School, Alta Vista Elementary School, & Sarasota Art Museum. This home gets extra points for its central location. Sarasota City Limits allow for great flexibility for short term rentals on Air BNB, VRBO and short term rentals. Located in the 1-week rental zone. No HOA! Close to the sun kissed beaches of Sarasota, downtown, cultural venues, Big Olaf Ice cream, Yoders Fresh Fruit and Vegetable Market, YMCA, and Locklear Park. Everything is just minutes away. Move quick. Don't miss out.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Brett Decklever (248-766-7571)
5883 WHISTLEWOOD CIR, SARASOTA, FL 34232
$485,000171 Days on yellowkey MLS ID: A4671389
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1530 Built: 1979 Tax: $5,067 (2024)Community: Ridgewood Estates 20Th AddSpa: NoSingle Family
Taxes:$5,067
Remarks: Welcome to 5883 Whistlewood, a centrally located Sarasota retreat, with no HOA, that blends everyday convenience with the best of Florida living. If you’ve been searching for a home that offers a relaxed, coastal lifestyle with quick access to everything Sarasota is known for, this is it. Live just 7.5 miles from downtown Sarasota, where world-class dining, shopping, and entertainment await. Enjoy easy evenings at spots like Ocean Prime, weekend strolls along the Bayfront, or spur-of-the-moment outings to the Farmers Market. When you’re craving beach time, Siesta Key, consistently ranked America’s #1 beach, is only 7 miles away, making sunrise walks, sunset sessions, and full beach days part of your weekly routine. Back at home, unwind in your private swimming pool or relax in the screened-in lanai overlooking a fully fenced backyard, perfect for pets, play, and peaceful afternoons outdoors. Inside, the home offers 4 bedrooms, giving you the flexibility to create guest space, a home office, or a hobby room. The location is ideal for those who value both privacy and connectivity. The neighborhood is quiet and established, yet you’re only 0.8 miles from I-75, making commutes smooth and travel effortless. Outdoor enthusiasts will love being just 2 miles from Urfer Family Park, with walking trails, playgrounds, and green space to enjoy year-round. Whether you’re looking for a primary residence, a seasonal escape, or a property that balances lifestyle with convenience, 5883 Whistlewood delivers a truly complete Sarasota experience, pool days, beach weekends, downtown nights, and a peaceful home base in the heart of town.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Traci Bolen (941-914-5159)
111 S PINEAPPLE AVE #1021, SARASOTA, FL 34236
$1,299,00023 Days on yellowkey MLS ID: A4688715
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1575 Built: 2019 Tax: $18,357 (2025)Community: Mark Sarasota CondoSpa: YesCondo
Taxes:$18,357
Remarks: Experience refined urban living in this beautifully updated residence, complete with two dedicated parking spaces, featuring two bedrooms, 2.5 baths, and a versatile bonus room. Thoughtfully designed with an open concept layout, the home seamlessly blends modern style and everyday functionality, enhanced by high end builder finishes and custom upgrades throughout. The flexible den, ideal as a library, media room, or home office, offers endless possibilities. At the heart of the home, the gourmet kitchen impresses with an induction cooktop, quartz countertops, custom backsplash, and under cabinet lighting, perfect for both everyday living and entertaining. The spacious owner’s suite serves as a private retreat, featuring direct terrace access, a large walk in closet, additional custom storage, and a spa inspired bathroom with dual vanities, an oversized countertop, and a glass enclosed walk in shower with a rain showerhead. Each bedroom includes its own en suite bath, and the additional half bath is both stylish and convenient for guests. Storage is thoughtfully maximized with custom built closets, cabinetry, and shelving throughout. Luxury upgrades include porcelain flooring, designer light fixtures, premium wireless ceiling fans, an Ecobee smart thermostat, and remote controlled Hunter Douglas window treatments. Residents also benefit from community EV charging stations. The expansive terrace offers ample room for outdoor dining and lounging, with sweeping views of downtown Sarasota and the bay, perfect for taking in stunning sunsets. Residents of The Mark enjoy exceptional amenities, including a stylish club room and lounge, a state of the art fitness center, and an outdoor entertaining area with grilling stations, fire pit, and a 65 foot heated saltwater pool and spa. Located in the heart of downtown Sarasota’s vibrant arts and dining district, the building offers 24 hour security and on site management. Built in 2019, The Mark is known for its sleek contemporary design and premier location just steps from Main Street’s boutiques, restaurants, and popular farmers market. Schedule your private showing today.
Listing Agent: Mairead Smialek (847-334-4848)
4530 ATWOOD CAY CIR #13, SARASOTA, FL 34233
$299,00030 Days on yellowkey MLS ID: A4688320
1 Days Off yellowkey (back on 4/8/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1804 Built: 1985Monthly Fee: $440 Tax: $3,757 (2024)Community: Center Gate Estate Vill 4Villa
Taxes:$3,757
Elementary School: Ashton Elementary
Remarks: Under contract-accepting backup offers. If you have been searching for a villa that actually lives like a home, this is it. 4530 Atwood Cay Circle is one of the most spacious and well-appointed villas available in all of Center Gate Estates, and it checks every box that is genuinely hard to find in this price range: three bedrooms, a two-car garage, 1,804 square feet of living space, a fully air-conditioned Florida room, and a turnkey fully furnished interior ready for you to move in and start living. Three-bedroom villas in Center Gate Estates are rare. Most buyers spend months searching for one. This is your chance to stop searching. The floor plan is open, airy, and thoughtfully designed around how people actually live. The split-bedroom layout provides genuine privacy, placing the primary suite on one side of the home and the two guest bedrooms on the other. Wood floors and stone countertops anchor the interior with a warm, updated aesthetic. The kitchen is well-equipped and flows naturally into the main living and dining areas, creating a connected, comfortable space ideal for everyday living and easy entertaining. The air-conditioned Florida room is a standout feature that sets this villa apart from the rest. Year-round comfort, natural light, and a peaceful view make it the kind of space you will use every single day, whether for morning coffee, afternoon reading, or evening conversation. It is not a screened lanai. It is genuine, climate-controlled living space that adds real usability to an already generous floor plan. The two-car garage provides the kind of storage, parking, and practicality that villa buyers consistently say they want and rarely find. In a community where single-car garages are the norm, this is a meaningful upgrade. The home comes fully furnished, so from the day you close, there is nothing left to do but enjoy. Every detail has been handled. Center Gate Estates delivers the maintenance-free Florida lifestyle in a quiet, well-kept community complete with a pool, lush greenbelts, and peaceful walking paths. The location is central Sarasota at its most convenient: minutes to Siesta Key Beach, close to Doctors Hospital, Bee Ridge Road shopping and dining, and quick access to I-75 for wherever life takes you next. Spacious. Rare. Turnkey. Priced to move. Schedule your showing today. Center Gate Estates. 4530 Atwood Cay Circle #13. Sarasota FL 34233
1600 KENILWORTH ST, SARASOTA, FL 34231
$795,000260 Days on yellowkey MLS ID: A4661230
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1748 Built: 2017 Tax: $7,188 (2024)Community: Johnson EstatesSingle Family
Taxes:$7,188
Remarks: Under contract-accepting backup offers. Nestled in one of Sarasota’s most tranquil neighborhoods near Oyster Bay and the Field Club. This custom-built 2021 home blends modern comfort with coastal charm. Every detail was thoughtfully designed to suit the lot, maximize natural light, and create a low-maintenance tropical retreat. Step inside the inviting entryway, and you’re immediately welcomed by an airy, sun-filled interior. The modern porcelain tile flows throughout, making upkeep a breeze and adding to the home’s bright, open feel. The chef-inspired kitchen features sleek Bosch refrigerator and dishwasher and an open layout, connecting effortlessly to the living area so family and friends are always part of the conversation. From the living room, oversized impact-rated sliding glass doors frame the tropical Areca Palms, while the surrounding paver walkways keep everything clean and manicured. The owners suite is a serene sanctuary, and the luxurious master bath is a true showstopper—featuring a deep soaking tub and a sleek modern wet room design typically reserved for far more expensive homes. This home was built to the most current building and storm codes, featuring a metal roof, impact windows, doors, and sliders, and a high efficiency German made electric tankless water heater. Positioned High and dry, firmly outside of any flood zones. The spacious laundry room keeps day-to-day living organized and effortless. Some additional features include spray foam insulation in the attic, a 30 amp circuit for RV or EV vehicle charging and hard wired security cameras for peace of mind. Convenience is one of the location’s best attributes Including Trader Joes, Publix , Local restaurants, boutiques, shops, not to mention the highly desirable Philippi Shores elementary, Sarasota High and so much more. Schedule your personal tour today.
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