Location: Sarasota
Do Not Show Listings
235 COCOANUT AVE #113C, SARASOTA, FL 34236
$799,00076 Days on yellowkey MLS ID: A4692996
1 Days Off yellowkey (back on 6/23/2026)
Bed: 3 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2310 Built: 2006 Tax: $11,743 (2025)Community: Marquee En VilleSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$11,743
Elementary School: Alta Vista Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Under contract-accepting backup offers. Located in the Theater District of Downtown Sarasota, this 4-story townhouse offers convenient access to dining, shopping, waterfront parks, and cultural venues. Featuring approximately 2,310 sq ft of living area (2,764 total sq ft), this 3-bedroom, 4.5-bath residence provides functional living space within a gated community. A private elevator services all levels, along with a wood staircase. The first floor includes an attached 2-car garage with overhead storage and a foyer with a flex room and full bath with shower, offering multiple potential uses such as office, fitness space, or additional sleeping area. The second level features an open-concept kitchen with granite countertops, stainless steel appliances, natural gas cooktop, breakfast bar, and an updated hood and ventilation system. The kitchen connects to the main living area and dining space, with a half bath on this level. The third level includes two-bedroom suites, including a primary bedroom with walk-in closet and en-suite bath, and a second bedroom with a private bath. The fourth level offers a bonus room with kitchenette, full bath, and access to outdoor space perfect for pets, plants, BBQ and outdoor sunning. Floor-to-ceiling windows provide natural light and views of the surrounding downtown area. This residence has the coveted corner location with more windows than other units. Gated entry points with coded access and since it’s the first unit easier in and out. Community amenities include gated access, heated pool/spa, and state-of-the-art fitness center. This desired location and community amenities provide a well-rounded downtown living experience—schedule your showing to explore this opportunity.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Heather Chase (941-320-3121)
1435 WESTWAY DR, SARASOTA, FL 34236
$11,900,00036 Days on yellowkey MLS ID: A4697230
Bed: 5 Bath: 7.0 Gar: 4 Liv Area Sq Ft: 5759 Built: 2013Monthly Fee: $21 Tax: $134,995 (2025)Community: Lido C/Lido ShoresSingle Family
Taxes:$134,995
Elementary School: Southside Elementary
High School: Sarasota High
Remarks: At the end of Westway Drive, where Lido Shores meets the open water of New Pass, 1435 Westway Drive occupies one of Sarasota’s most extraordinary waterfront settings. Private, gated, and set on a double lot, the estate captures sweeping views across New Pass toward Longboat Key while offering direct deepwater access to the Gulf of Mexico and Sarasota Bay. This is the rare property that delivers every element of elevated coastal living in one address: boating, privacy, architectural presence, beach access, proximity to St. Armands Circle, and a level of land rarely found on Lido Key. Designed by Brian Phipps and built in 2013, the British West Indies–inspired residence blends timeless coastal architecture with modern luxury. Inside, expansive living spaces are framed by tall ceilings, walls of glass, rich wood flooring, custom millwork, and a natural connection to the water beyond. The great room opens to the waterfront terraces, creating an effortless flow between interior comfort and outdoor living. The kitchen is designed for both daily living and large-scale entertaining, with premium appliances including Sub-Zero and Wolf, generous stone surfaces, custom cabinetry, and an open connection to the main living and dining areas. Whether hosting guests after a day on the boat or enjoying a quiet evening overlooking the water, the home feels equally suited to celebration and retreat. With five bedrooms, two primary suites, and elevator service, the floor plan offers rare flexibility for owners, family, and extended guests. The upper-level owner’s retreat is a private sanctuary, complete with a sitting area, wet bar, wine refrigeration, espresso station, study, dual walk-in closets, and a terrace overlooking New Pass, the Gulf, and the lights of Longboat Key beyond. The outdoor living experience is exceptional. Covered terraces, a summer kitchen, resort-style pool, waterfall feature, and waterfront lounge spaces create a private setting designed around the view. The dock includes a 24,000-lb boat lift and additional jet ski lift, placing premier boating waters directly at your door. From here, New Pass provides immediate access to the Gulf, Sarasota Bay, Longboat Key, and the surrounding barrier islands. What truly sets the property apart is its scale. The estate spans approximately three-quarters of an acre, including an adjacent parcel that has been transformed into a lush private garden with mature landscaping, open lawn, fire pit, pond, cascading waterfall, and meandering paths. It gives the home a sense of arrival and breathing room that is almost impossible to recreate in this location. With its own gated access and generous dimensions, this portion of the property also offers future flexibility for a guest house, wellness pavilion, additional structure, or further reimagining, subject to applicable approvals. Lido Shores remains one of Sarasota’s most coveted coastal enclaves, known for its architectural pedigree, quiet streets, private beach access, and rare positioning between the Gulf, New Pass, St. Armands Circle, downtown Sarasota, and Longboat Key. Residents enjoy the privacy of a true neighborhood while remaining moments from dining, shopping, boating, beaches, and culture. Previously recognized as an HGTV Ultimate House Hunt winner for waterside living, 1435 Westway Drive is more than a waterfront residence—it is a private Sarasota estate with presence, scale, and a setting that cannot be duplicated.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Skrzypkowski (941-328-8307)
2098 PALM VIEW RD, SARASOTA, FL 34240
$944,000173 Days on yellowkey MLS ID: A4680898
2 Days Off yellowkey (back on 6/23/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3732 Built: 2004Monthly Fee: $47 Tax: $5,785 (2025)Community: Oak Ford Golf ClubSpa: YesSingle Family
Taxes:$5,785
Elementary School: Tatum Ridge Elementary
Middle School: McIntosh Middle
Remarks: Under contract-accepting backup offers. If you're looking for room to breathe, privacy, and water views, look no further than 2098 Palm View Road. Set on nearly an acre in the private, deed-restricted community of Oak Ford, this updated residence offers a rare blend of openness and comfort. Overlooking 2 tranquil ponds, the property enjoys a peaceful, natural setting and offers more than 3,700 sf of living space. Recent improvements include a new roof in 2023, PGT impact windows and doors, and newer appliances, further enhancing the home’s appeal and move-in readiness. The 4 bedroom, 3 bathroom layout is designed for both comfortable everyday living and effortless entertaining. Vaulted ceilings and an open floorplan enhance the sense of scale, while PGT impact windows and doors provide added protection and efficiency. An oversized foyer creates a welcoming first impression and leads into the main living areas, where unique polished concrete flooring, a central gathering space, and a well-appointed kitchen with a gas range and island come together beautifully. The kitchen features custom solid-wood cabinetry, stone countertops, stainless steel appliances, an island with storage and seating, and generous prep space. The first-floor primary suite creates a private retreat with direct access to the screened outdoor patio and living area. Two additional bedrooms are located on the main level, while the second floor offers an expansive fourth bedroom or flexible bonus space ideal for a home office, gym, media room, or studio. Outdoor living is a standout feature of this expansive property. The screen-enclosed, heated pool and spa overlook a south-facing backyard with ample space for gardening or playing sports, with pond and lush preserve views.. A waterside fire-pit seating area and a shaded swing add additional inviting destinations and the perfect spots to end the day. This nearly one-acre homesite also includes an oversized 3-car garage and an extended driveway, allowing ample room for parking and storage. Oak Ford is known for its oversized parcels, custom-built homes, and peaceful setting. Just a short drive west, Waterside Place and Fruitville Commons offer upscale eating and activities. Just a little further, Downtown Sarasota offers acclaimed dining, arts, and waterfront experiences, while St. Armands Circle and the Gulf beaches — including Siesta Key, Lido Key, and Longboat Key — provide some of the area’s most celebrated coastal attractions. In this gorgeous home, you have access to everything Sarasota has to offer, and a sanctuary to retreat to.
Listing Agent: Kelly Rosenberg (941-961-4948)
1035 SEASIDE DR #308, SARASOTA, FL 34242
$2,550,00084 Days on yellowkey MLS ID: A4692379
REDUCED by $50,000 (1.9%) on 06/23/2026
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1646 Built: 2023 Tax: $21,387 (2025)Community: Ten35 SeasideSpa: YesCondo
Taxes:$21,387
Elementary School: Phillippi Shores Elementary
Middle School: Sarasota Middle
Remarks: Gulf-Front Luxury with Investment Appeal Experience elevated beachfront living at Ten35 Seaside, a boutique Gulf-front community on the quiet southern end of Siesta Key. This beautifully designed 2-bedroom, 2.5-bath residence offers private beach access, resort-style amenities, and strong luxury rental potential. The open-concept layout features Wolf and Sub-Zero appliances, custom cabinetry, sleek coastal finishes, and spacious living areas filled with natural light. Sliding glass doors open to a private terrace perfect for enjoying Gulf breezes and sunset skies. The primary suite offers a spa-style bath and walk-in closet, while the guest suite includes built-in bunk beds for added flexibility and rental appeal. Residents enjoy a beachfront pool and spa, private cabanas, fitness center, and direct access to Siesta Key’s world-famous beaches — all just minutes from Siesta Key Village and downtown Sarasota. Ideal as a luxury beachfront retreat, full-time residence, or income-producing coastal investment property. Buyer to verify rental policies, restrictions, and all room dimensions.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Rex Glasson (941-587-6135)
7559 QUINTO DR, SARASOTA, FL 34238
$390,000145 Days on yellowkey MLS ID: A4684986
REDUCED by $5,000 (1.3%) on 06/09/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1534 Built: 2003Monthly Fee: $476 Tax: $2,904 (2025)Community: VillagewalkVilla
Taxes:$2,904
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. Virtually Staged. ***PRICE REDUCTION *** Best Opportunity to live in Village Walk/ Priced to Sell! Welcome to this beautifully maintained 2 bedroom, 2 bathroom villa in the highly sought-after VillageWalk in Sarasota, Florida, offered at $390,000 with BRAND NEW AC unit placed 3/2/2026. This move-in ready home with one original owner features an inviting open-concept floor plan filled with abundant natural sunlight. The spacious split-bedroom layout provides privacy for both owners and guests. The primary suite includes a private en-suite bath and generous closet space, and the comfortable guest bedroom and bath are ideal for visitors or a home office. Enjoy peaceful mornings or relaxing evenings from your private outdoor space, all while benefiting from low-maintenance villa living. VillageWalk is a guard-gated, resort-style community known for its scenic lakes, and miles of walking and biking trails. Residents enjoy an impressive array of amenities including a heated lagoon-style pool and separate lap pool, tennis courts, pickleball courts, a state-of-the-art fitness center, clubhouse with event space, on-site café and boutique shops, and 24-hour security. Conveniently located just minutes from Siesta Key Beach, top-rated dining, shopping, and medical facilities, this home offers the perfect combination of privacy, lifestyle, and accessibility in one of Sarasota’s most desirable communities.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: David Allison (954-815-4378)
1558 4TH ST #216, SARASOTA, FL 34236
$750,000301 Days on yellowkey MLS ID: A4665163
REDUCED by $25,000 (3.2%) on 05/24/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1023 Built: 2024Monthly Fee: $994 Tax: $8,489 (2025)Community: Zahrada 2Condo
Taxes:$8,489
Remarks: **Motivated Seller in the Exquisite Rosemary District!** Experience Sarasota at full speed in this chic, Rosemary District pied-à-terre! Step outside and you’re instantly surrounded by the very best of downtown and the vibrant Rosemary District—art galleries, theaters, boutiques, cafés, waterfront parks, and world-famous Gulf beaches just minutes away. This is the heartbeat of Sarasota, and you’re living right in the middle of it. Be the first to call this brand-new, never-lived-in 2-bedroom, 2-bath modern home your own. Chef’s kitchen with glittering quartz counters, stainless-steel appliances, and designer two-tone cabinetry with lacquered uppers. Slide open the glass doors and step into your private courtyard oasis—the perfect spot to enjoy your morning coffee or cocktails beneath the stars. Head upstairs to your loft bedroom retreat, complete with city views, an ensuite bath, and a custom-built closet. The living space is drenched in natural light thanks to an enormous two-story window, highlighted by a vaulted ceiling. Beautiful tile flooring runs throughout, adding style and easy-care comfort. Enjoy secure, under-building parking for one vehicle, plus abundant street parking right outside your door. This home is the perfect blend of luxury, convenience, and urban excitement!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-748-6300)
Listing Agent: Ian Schmitzerle (734-664-5466)
280 GOLDEN GATE PT #600, SARASOTA, FL 34236
$5,500,000288 Days on yellowkey MLS ID: A4668258
REDUCED by $100,000 (1.8%) on 06/02/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4101 Built: 2016 Tax: $72,785 (2025)Community: AquaSpa: YesCondo
Taxes:$72,785
Remarks: NO CONDO FEES FOR 2026!!! Discover the pinnacle of direct bayfront excellence blending sculptural modern form with dazzling water views. This full-floor 3-bedroom + office/den or 4th bedroom residence at AQUA, one of the only residential towers in Southwest Florida designed by highly acclaimed award-winning architect, Guy Peterson, of the Sarasota School of Architecture, is one of only eight in the most exclusive boutique building found on Golden Gate Point. Perched on the sixth floor with 180° views of Sarasota Bay and the iconic Ringling Bridge, this home offers a level of elegance and customization rarely found—even in new construction. From the moment you step off your private elevator into the foyer, the residence unfolds with simple, clean lines spotlighting floor-to-ceiling 10-foot glass walls which frame the Bay & Sunsets like living artwork. More than $500,000 in curated upgrades elevate the interiors, transforming this barely lived in 4,100+ sq ft space into a truly one-of-a-kind lifestyle rarely found in Sarasota’s market. Open-concept layout lives like a single-family home with distinct entertaining areas, a stunning waterfront dining room, and a bespoke wet bar. Chef’s kitchen is a study in form and function, seamlessly integrated into the living space while offering top-tier appliances and finishes: Wolf cooktop and ovens, 2 Miele dishwashers, Sub-Zero refrigerator, Cuisines Laurier cabinetry with a 9 ft expansive island topped with striking Cielo quartzite. Private primary suite is designed as a serene escape, featuring stunning water views, custom walk-in closets uniquely designed with two separate individual sections of sleek Cuisimax poly-gloss doors and packing station. Elevated features in the spa-style bathroom include dual vanities topped with striking azure crystal marble, a soaking tub, and a large glass-enclosed shower Two generous guest suites offer en-suite privacy, while a fourth bedroom currently serves as a sleek office. With discreet concierge services found only in a 5-star boutique style building, Aqua offers an enclosed oversized private two-car garage with an EV charging station & dehumidifier, private boat dock that accommodates 36' boat + flat kayak lift, temperature-controlled wine storage/wine tasting room, fitness studio, heated pool and spa and meeting room. Be part of vibrant downtown living in a secluded quiet location.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
2232 GROVE ST, SARASOTA, FL 34239
$2,350,000266 Days on yellowkey MLS ID: A4670786
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3800 Built: 2025 Tax: $9,281 (2024)Community: Blossom BrookSpa: YesSingle Family
Taxes:$9,281
Tax Year: 2024
Remarks: Under Construction. Imagine waking up to the soft glow of Florida sunlight streaming through expansive windows, the aroma of morning coffee drifting from your open-concept kitchen, and laughter echoing from your backyard oasis. Welcome to your future home at 2232 Grove Street — a place where innovative design meets effortless family living. Nestled in the heart of Sarasota, this custom modern residence has been thoughtfully envisioned for both comfort and connection. The design balances clean architectural lines with natural warmth — soaring ceilings, elegant finishes, and light-filled living spaces that open seamlessly to outdoor areas. Here, every detail invites gathering and togetherness — from the spacious chef’s kitchen perfect for Sunday breakfasts, to the inviting great room where memories unfold. Step outside to a private backyard oasis, backing up to large single-family parcels that ensure peace and privacy. There’s room for play, and for the simple joys of Florida living. Whether it’s hosting friends under the stars or watching the kids chase fireflies at dusk, this home was made for moments that matter. Just minutes from downtown Sarasota, top-rated schools, and Siesta Key’s pristine beaches, 2232 Grove Street offers more than a home — it’s the foundation for your next chapter. Write your story here, where modern luxury and approachable comfort are seamles.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Rudy Dudon (941-234-3991)
300 S PINEAPPLE AVE #302, SARASOTA, FL 34236
$1,495,00084 Days on yellowkey MLS ID: A4691974
REDUCED by $100,000 (6.3%) on 06/15/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2291 Built: 2016 Tax: $19,826 (2025)Community: SansaraSpa: NoCondo
Taxes:$19,826
Remarks: Boutique downtown living takes on a new level of sophistication at Sansara, an exclusive 10-story building with only 17 private residences in one of Sarasota’s most walkable and vibrant locations. Just moments from Burns Court’s cafés, eclectic boutiques, galleries, and the Sarasota Bayfront, this address offers both convenience and a sense of quiet retreat. Residence 302 captures a peaceful, elevated perspective with views of tropical greenery, the glistening pool, and the city skyline beyond. Encompassing nearly 2,300 SF, the home is thoughtfully designed with expansive walls of glass that invite in abundant natural light, rich hardwood flooring, tailored cabinetry, elevated lighting selections, and automated window treatments. The kitchen serves as a stylish centerpiece, appointed with sleek European cabinetry, quartz countertops, premium Bosch appliances plus wine refrigerator, and a spacious island ideal for gathering. The open-concept living area extends effortlessly to a private terrace; an inviting space to start the day or relax in the evening while overlooking the pool below. A well-designed split floor plan provides both comfort and privacy. The primary suite is a serene escape with terrace access, custom walk-in closet, and a spa-like bath featuring dual vanities and a walk-in shower. Two additional guest suites, one perfectly suited for a home office or den, offer versatility for a variety of lifestyles. Additional highlights include impact-rated windows and 10-foot disappearing sliders, multiple outdoor spaces, custom dry bar for effortless entertaining, generously sized laundry room with storage, customized closets, and secure elevator access. Residents of Sansara enjoy a collection of boutique amenities, including a heated saltwater pool and spa, cabana areas, fire pit lounge, outdoor kitchen and grill, a fitness studio, and secure building access. All designed to complement a relaxed yet refined downtown lifestyle. The residence is offered with the option to be sold partially furnished.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Linda Driggs (941-374-2920)
5015 BARRINGTON CIR #201, SARASOTA, FL 34234
$179,90068 Days on yellowkey MLS ID: A4694338
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1204 Built: 1982Monthly Fee: $610 Tax: $3,221 (2025)Community: Barrington WoodsVilla
Taxes:$3,221
Remarks: Fall in love with this spacious, updated 2 bedroom/2 bathroom villa in the wooded solitude community of Barrington Woods. This maintenance free unit is nestled in Sarasota’s art and museum district, minutes to downtown Sarasota and gulf beaches. New A/C, interior private laundry room, open floor plan, vaulted ceilings, granite countertops, stainless steel appliances, large eat-in kitchen, breakfast bar, lots of cabinetry, pantry, tile floors throughout and wood flooring in the primary bedroom (large walk-in closet). Screened entry/lanai with your own covered parking space along with plenty of guest parking and a community pool. Located 1 mile to Sarasota/Bradenton International Airport and New College of Florida/USF campuses, Ringling Museum of Art, Asolo Theatre, Sarasota Ballet and Sarasota’s bay front. Minutes to Centennial Park boat ramp, Van Wezel Performing Arts, area beaches, downtown Sarasota and all of the cultural activities, shopping and dining that it has to offer! This quiet and peaceful end residence has been freshly painted and is ready for you to move into.
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Wendy Lewis (941-993-5708)
9296 STARRY NIGHT AVE, SARASOTA, FL 34241
$2,090,000155 Days on yellowkey MLS ID: A4683429
REDUCED by $110,000 (5.0%) on 06/23/2026
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4877 Built: 2022Monthly Fee: $251 Tax: $18,536 (2025)Community: Cassia At Skye RanchSpa: YesSingle Family
Taxes:$18,536
Elementary School: K-8 At Clark And Lorriane
High School: Riverview High
Remarks: Experience elevated living in the highly sought-after Skye Ranch community of Sarasota. Perfectly positioned on Starry Night Avenue, this expanded Beacon Model offers an impressive 4,877 square feet under air across two thoughtfully designed levels, showcasing refined finishes, extensive upgrades, and exceptional attention to detail throughout. Meticulously maintained and beautifully appointed, this four-bedroom residence features four full baths and two half baths, including three private ensuite bedrooms and a fourth bedroom with Jack-and-Jill bath access. The main living areas are enhanced by soaring ceilings, elegant flooring, and expansive open spaces designed for both everyday comfort and effortless entertaining. At the heart of the home, the gourmet kitchen is a culinary showpiece, appointed with a Monogram six-burner gas range top with pot filler, double dishwashers, a separate beverage refrigerator with pass-through to the formal dining room, a generous quartz-topped island with touchless faucet, walk-in pantry, and a casual dining area overlooking the stunning outdoor living space. The main level also offers a private office and dedicated media room, providing flexibility for work, relaxation, or recreation. The spacious primary suite provides the perfect retreat to unwind, offering direct access to the lanai and pool area. Your private retreat area is complimented by two custom walk-in closets and a spa-inspired bath designed for relaxation. Upstairs, the second level is ideal for guests or multigenerational living, featuring a spacious bonus room with wet bar, beverage refrigerator, dishwasher, half bath, and a private ensuite bedroom. Outdoor living is truly resort-inspired. The expansive lanai with travertine flooring frames a graciously sized pool and spa with built-in waterfall, firepit, and sunshelf. A fully equipped summer kitchen and serene preserve views create a private, tranquil setting perfect for entertaining or relaxing year-round. Additional highlights include a spacious laundry room and a three-car garage offering ample storage. Ideally located near The HUB Amenity Center and the new Skye Ranch School, residents enjoy access to exceptional community amenities including a resort-style pool, fitness center, clubhouse, café, dog park, scenic trails, sports courts, playgrounds, and a vibrant calendar of events. Convenient to I-75, shopping, dining, and Sarasota’s renowned Gulf Coast beaches. A remarkable opportunity to embrace refined Florida living in one of Sarasota’s most desirable communities.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Judy Wright, Pa (941-232-8041)
3440 GULFMEAD DR, SARASOTA, FL 34242
$12,900,000187 Days on yellowkey MLS ID: A4679384
REDUCED by $1,050,000 (7.5%) on 06/23/2026
Bed: 5 Bath: 5.0 Gar: 6 Liv Area Sq Ft: 6596 Built: 2008 Tax: $58,421 (2025)Community: Gulfmead EstatesSpa: NoSingle Family
Taxes:$58,421
Remarks: Discover a rare opportunity to enjoy pristine Gulf views, aquamarine waters, and a deep-water dock on the very North end of Siesta Key, just minutes to downtown Sarasota. One of Siesta Key’s most stunning and secluded waterfront sites — a residence offering a rare combination of historic significance, panoramic views of Big Pass, and exceptional structural integrity. Located approximately 200 feet south of civic leader Henry Higel’s early 20th-century Higelhurst Hotel, the pioneering developer’s beloved coastal breezes still beckon family and friends to enjoy swimming, water sports, boating, fishing, shoreline picnics, and direct, no-bridge access to the sparkling Gulf. Multiple covered porches and expansive windows provide front-row views of vivid sunsets and frolicking dolphins. Named for its pineapple stair finials symbolizing welcome, the Pineapple House was built in 2008 with an engineer-homeowner’s meticulous eye for detail. Constructed on pilings and grade beams, the home is set on a 31,293-square-foot lot and encompasses 6,596 square feet under air, with more than 13,000 total square feet. Designed by Diane Weinman with a refined Boca Grande aesthetic and built by ML Collingwood, the dwelling projects enduring quality, thoughtful engineering, and elevated coastal living. Enter through the impressive double doors to a sensual treat of symmetry and light. Main-level windows crowned with transoms frame views of the tropical blue sky. Walnut engineered flooring, Jerusalem stone, eight-foot doors, custom millwork, and generous closets enhance both functionality and beauty throughout. Scaled to feel both warm and elegant, the interiors are enriched with refined finishes and thoughtful architectural detailing. Living spaces encompass a formal dining room with butler’s pantry, living room, bookcase-lined library or sitting room, private office with built-in desk and cabinetry, dedicated home gym, and a flexible gathering room. A second primary or guest suite on the main level offers a private sitting area, breakfast bar, screened porch, and picture-perfect water views. An elevator conveniently serves all three floors. The chef’s kitchen anchors the main living areas with honed granite countertops, Sub-Zero appliances, custom Campbell cabinetry, and a walk-in pantry, opening to casual dining spaces and sun-filled outdoor porches. Upstairs, the primary suite is a tranquil retreat featuring a spa-inspired bath, oversized walk-in closet, shaded terrace, and outdoor shower. The expansive dock features two boat lifts: one 22,000-pound lift suitable for a 32- to 36-foot vessel and a second 10,000-pound lift. A humidity-controlled four-car tandem garage and a separate two-car garage accommodate up to six vehicles along with extensive marine and recreational gear. Solar panels and a 30kW generator underscore the home’s focus on energy efficiency and resilience. Outdoor living is highlighted by a 20,000-gallon heated saltwater lap pool surrounded by Shellcrete patios and Ipe decking. A perched beach with fire pit and swings welcomes gatherings overlooking Big Pass, while a 75-foot rear setback ensures privacy within a lushly landscaped yard. Rich in history, resilient and luxurious, intimate and refined, this is Sarasota waterfront living at its most authentic and coveted. Photos 1 and 2 reflect the new colors that the home is being painted.
Listing Agent: Jennifer Linehan (941-266-7555)
2121 33RD ST, SARASOTA, FL 34234
$189,90081 Days on yellowkey MLS ID: O6406141
REDUCED by $10,000 (5.0%) on 06/23/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 816 Built: 1960 Tax: $1,308 (2025)Community: Newtown FarmsSingle Family
Taxes:$1,308
Remarks: Well maintained Sarasota 3BR/1BA block home featuring a brand new permitted well and pump, approximately 11-year-old roof, fresh interior and exterior paint, updated fixtures, reglazed tub and shower tile, attached laundry room, and large screened lanai. The home features a functional layout, spacious backyard, good windows, plumbing, electrical, and HVAC, along with very low annual property taxes that help keep ownership costs down. Property is on well and septic. Tenant currently in place through February 2027 paying approximately $1,700/month, providing flexibility for future plans or continued rental income. Please do not disturb tenant.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
1001 POINT OF ROCKS RD #208, SARASOTA, FL 34242
$1,195,00036 Days on yellowkey MLS ID: A4697514
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1200 Built: 1988 Tax: $10,536 (2025)Community: Siesta Sands ResortCondo
Taxes:$10,536
Remarks: Gulf view condominium at the Siesta Sands Resort, at the southern tip of world-famous Crescent Beach on Siesta Key. This second-floor end unit, featuring two bedrooms, two baths and two private balconies, has been completely renovated, tastefully decorated and furnished, with in-unit laundry, a reserved parking space and a nice view of the blue waters of the Gulf, as well as a good view of one of the resort’s pools. The resort-style condominium is on a beautiful private beach featuring what has been rated as the whitest sand, consisting of 99 percent pure quartz, which stays cool under your feet. Residents of Siesta Sands enjoy an impressive array of resort-style amenities, including beach service for lounge chairs and umbrellas, two heated pools, community Wi-Fi, a poolside gazebo, gas grills, an exercise room and serene bamboo lounge. This boutique beachfront community offers a secluded, gated retreat with only 31 units and exclusive private beach access to Crescent Beach. The unbeatable location places you near Siesta Key's South Village. Siesta Sands allows weekly rentals and has an excellent on-site rental office to keep the condominium rented when not being utilized for personal use. The Point of Rocks is an area known for its coral formations and marine life, ideal for fishing or snorkeling. This resort condominium is offered turnkey furnished with solid rental history and further bookings in place. This is must-see. Don’t miss out.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Ziad Sleit (941-928-5493)
4211 64TH AVE E, SARASOTA, FL 34243
$465,00036 Days on yellowkey MLS ID: A4697827
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1710 Built: 2006Monthly Fee: $577 Tax: $5,325 (2025)Community: Cascades At Sarasota Ph IiiaSingle Family
Taxes:$5,325
Remarks: Two bedrooms, a den, and water views in one of Sarasota's most active 55+ communities — and no CDD fees. This home in Cascades at Sarasota has been well cared for and is completely carpet-free, with tile and luxury vinyl plank throughout. The layout works: an eat-in kitchen with updated finishes, a separate dining area, two comfortable bedrooms, and a den that works well as a home office or hobby room. The extended screened lanai has water views, sunsets, and enough room to actually entertain — not just two chairs and a side table. Cascades is a gated, maintenance-free community with lawn care included and no CDD fees. The 25,000-square-foot clubhouse was recently renovated and includes a heated indoor-outdoor pool, fitness center, banquet hall, six Har-Tru tennis courts with a full-time pro, pickleball, bocce, and an arts and crafts room with two pottery kilns. There's a full activity calendar if you want it, or you can keep to yourself — the community supports both. Location-wise, you're about 15 minutes from downtown Sarasota, the Ringling Museum, and Selby Gardens. Siesta Key, Lido Key, and Longboat Key are all within easy reach. UTC Mall and St. Armands Circle are close for shopping and dining, and Sarasota International Airport is convenient for traveling.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Dawn Merrill (941-915-7126)
9540 HIGH GATE DR #1411, SARASOTA, FL 34238
$460,00039 Days on yellowkey MLS ID: A4696292
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1661 Built: 1996 Tax: $2,993 (2025)Community: Stoneybrook Veranda Greens 1Spa: YesCondo
Taxes:$2,993
Remarks: Impressive 1ST floor ABBEY model, in sought after Stoneybrook Golf & Country Club in Palmer Ranch! Entire condo has been updated to today's designer tastes. And to make it even more desirable...all the windows and glass doors are HURRICANE IMPACT for extra peace of mind and energy efficiency. There are views from every window as this is an END unit, so you can see all of the #4 tee boxes from different windows of the home and amazing, and expansive views from the the back lanai of the 4th hole and lake, where nature abounds with birds, and wildlife. The impact glass secures peace and quiet inside, and brings in loads of natural light. Windows are adorned with classic plantation shutters and shades. The updated kitchen is stunning, showcasing all granite counters, tiled back splash, soft close drawers, SS appliances and an eat-on bar for entertaining guests or sit at the casual dinette overlooking yet another tiled and screened in lanai to relax and enjoy the fresh air all year round. Both bathrooms have been tastefully updated with walk-in, tiled glassed showers, and raised stone vanities. The thoughtful split-bedroom floor plan provides privacy for both owners and guests, while the DEN offers flexibility as a home office, reading room, or additional guest space, and enjoys a double door for more privacy. Additional highlights include a detached one-car garage with plenty of storage for your golf and beach gear. Veranda Greens has its own heated pool and grill area just steps out your front door, this is the ease of first-floor living with no stairs! Stoneybrook Golf and Country Club just completed their new 18 hole golf course designed by Arthur Hills and Kipp Schulties and is said to be one of the best on the West Coast! Other top-notch amenities include Lighted Har-Tru tennis/pickle ball courts, pro-shop, well-equipped fitness center, bocce court, putting greens, driving range, fitness studio, sharing library, additional heated pool/spa, full service restaurant/bar, meeting rooms, catering facility, outdoor dining patio, walking/biking trails, fishing, planned activities like yoga, mahjong, line dancing, and so much more! Stoneybrook Golf and Country Club is a prime location close to the Legacy Trail, area Beaches, Costco, Lowes, restaurants and all Sarasota and Venice has to enjoy! Experience the perfect blend of comfort, style, and resort-style living—schedule your private showing today!
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-556-2150)
Listing Agent: Julie Froeschle (941-228-6405)
5285 TWINFLOWER LN, SARASOTA, FL 34233
$614,90036 Days on yellowkey MLS ID: A4697830
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2231 Built: 2019Monthly Fee: $212 Tax: $5,997 (2025)Community: Reserve/HonoreSingle Family
Taxes:$5,997
Elementary School: Ashton Elementary
Remarks: Virtually Staged. Welcome to 5285 Twinflower Lane, a beautifully maintained and thoughtfully upgraded home in the highly desirable Reserve at Honore community. Built in 2019, this 3-bedroom, 2-bath residence offers 2,231 square feet of modern living space designed for both everyday comfort and effortless entertaining. From the moment you enter, you'll appreciate the bright, open-concept floor plan, soaring 10 to 11-foot ceilings, and luxury vinyl flooring that flows throughout the main living areas. The spacious kitchen serves as the heart of the home, featuring elegant quartz countertops, abundant cabinetry, and ample workspace for meal preparation, gatherings, and entertaining guests. The generous living and dining areas are filled with natural light and seamlessly connect to the outdoor living space, creating an inviting indoor-outdoor lifestyle that Florida homeowners love. The primary suite provides a private retreat with ample space to relax, while two additional bedrooms offer flexibility for family, guests, a home office, or hobby room. What truly sets this home apart is its impressive list of upgrades focused on efficiency, comfort, and peace of mind. Solar panels help reduce energy costs, while a whole-home generator provides dependable backup power during storms and unexpected outages. Additional enhancements include a blue-light HVAC purification system designed to improve indoor air quality, a 6-foot PVC privacy fence surrounding the backyard, and an extended lanai that creates the perfect setting for outdoor dining, entertaining, or simply enjoying the Florida sunshine. The exterior offers attractive curb appeal, a spacious 2-car garage, and a private backyard with peaceful patio views. Major systems reflect the home's newer construction, including a 7-year-old roof and 7-year-old air conditioning system, allowing buyers to enjoy the benefits of modern building standards and reduced maintenance concerns. Located in Reserve at Honore, this home places you close to shopping, dining, parks, top-rated schools, medical facilities, and the many attractions that make Sarasota one of Florida's most sought-after places to live. Whether you're searching for a primary residence, seasonal retreat, or move-in-ready home with valuable upgrades already in place, 5285 Twinflower Lane delivers the ideal combination of style, functionality, energy efficiency, and location. Don't miss this opportunity to own a newer Sarasota home featuring solar power, whole-home generator protection, an extended lanai, privacy fencing, and modern finishes throughout. Schedule your private showing today and experience everything this exceptional property has to offer.
Listing is courtesy of: HARRY ROBBINS ASSOC INC (941-924-8346)
Listing Agent: Emerson Robbins (941-404-0382)
2629 WATERFRONT CIR, SARASOTA, FL 34240
$1,199,00036 Days on yellowkey MLS ID: A4696784
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2828 Built: 2026Monthly Fee: $352 Tax: $3,070 (2025)Community: Monterey/Lakewood RanchSpa: NoSingle Family
Taxes:$3,070
Remarks: **Rare Never-Occupied Lakefront Selby in Monterey at Lakewood Ranch** Experience a rare ready-now opportunity in Monterey at Lakewood Ranch with this never-occupied Toll Brothers Selby. This 4-bedroom, 3.5-bath Transitional-style residence offers the appeal of new construction without the current build wait. Set on a premium lakefront homesite with no neighbor directly behind, the home offers a peaceful waterfront backdrop and a greater sense of privacy than many traditional homesites. For buyers seeking immediate ownership in Monterey, this property presents a compelling opportunity in a community where no quick move-in homes are currently available. The Selby floor plan was designed for beauty, function, and sophistication, with the refined flow luxury buyers expect. A grand foyer creates a memorable first impression and leads into an open great room designed for gathering, natural light, and everyday comfort. The kitchen overlooks the casual dining area and great room, creating a central living space that feels equally suited for entertaining, hosting guests, or enjoying quiet evenings at home. A large center island, generous cabinet and counter space, and walk-in pantry further enhance the kitchen’s livability. The primary suite offers a private retreat with dual walk-in closets and a relaxing bath featuring dual sinks, a luxe shower, linen storage, and a private water closet. Two secondary bedrooms include roomy closets and share a hall bath, while an additional secondary bedroom features a walk-in closet and private bath, creating excellent flexibility for guests, family, or work-from-home needs. The covered lanai extends the home’s living space outdoors and is accessed from the great room through multi-slide doors, allowing the lakefront setting to become part of daily living. Premium selections include an alternate kitchen layout, epoxy-coated garage floor, whole-house gutters, spray foam insulation, masonry core foam insulation package, pool prep package, and outdoor kitchen prep package. Monterey at Lakewood Ranch is a private gated Toll Brothers community designed around luxury homes, natural Florida ponds and lakes, and an elevated amenity lifestyle. Future community amenities are planned to include a resort-style pool, tennis courts, pickleball courts, fitness center, walking trails, dog park, open green space, and more. Located within the highly regarded Lakewood Ranch area, Monterey offers access to the broader lifestyle the region is known for, including nearby dining, shopping, recreation, events, golf, polo, and Gulf Coast beaches. For the buyer who wants a never-occupied Toll Brothers home, lakefront setting, no rear neighbor, documented upgrades, and the ability to move without waiting for a future build, this Selby residence is an exceptional opportunity in Monterey at Lakewood Ranch.
Listing is courtesy of: QUARTZ COAST REALTY INC (941-504-3874)
Listing Agent: Joy Eakins (417-612-1491)
5830 MIDNIGHT PASS RD #3, SARASOTA, FL 34242
$649,00036 Days on yellowkey MLS ID: A4697756
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 728 Built: 1960 Tax: $3,964 (2025)Community: Jamaica RoyaleVilla
Taxes:$3,964
Remarks: Wonderful gulf side attached villa in an all ground level association, so no milestone inspections required. This completely updated, open floor plan. Upgrades galore!! Fantastic rental history! The HOA installed a new roof on the property in 2023, too! Jamaica Royale allows short term rentals so this could be a great investment property or keep it for your own second home. This is the closest gulf side weekly rental property to the main public beach offering 3 swimming pools, grilling stations and shuffle board. Make this great property yours today at a value!
Listing is courtesy of: TIDELINE REAL ESTATE BROKERS (941-587-1669)
Listing Agent: Steve Cavanaugh (941-587-1669)
6140 MIDNIGHT PASS RD #606, SARASOTA, FL 34242
$1,279,00065 Days on yellowkey MLS ID: A4694184
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1521 Built: 1967Monthly Fee: $1,354 Tax: $13,588 (2025)Community: Horizons WestSpa: YesCondo
Taxes:$13,588
Middle School: Brookside Middle
Remarks: Nestled on the renowned shores of Siesta Key, Horizons West offers a truly exceptional waterfront living experience where breathtaking panoramic views and unforgettable sunsets become part of everyday life. This meticulously cared-for two-bedroom, two-bathroom residence, elevated on the sixth floor, delivers unparalleled luxury and privacy in a home that has never been in a rental program, resulting in exceptionally minimal wear and tear. Following a comprehensive top-to-bottom renovation that stripped the unit to its concrete box, every inch of this residence reflects the pride of true ownership with timeless, sophisticated design. The gourmet kitchen and bathrooms feature custom Harlan solid wood cabinetry sourced from Indiana, sleek granite countertops, and a premium suite of KitchenAid stainless steel appliances. Modern infrastructure is seamlessly integrated throughout, including Cat 6 data outlets, a commercial-grade PakEdge Wi-Fi router, and a whole-home surge protector. Comfort is guaranteed with a brand-new HVAC system installed in July 2025, complete with an air scrubber for active air purification. The home is an audiophile’s dream with a built-in multi-zone sound system featuring Vienna Acoustics speakers and a Marantz receiver. Elegant touches abound, from recessed LED and runway lighting to motorized Hunter Douglas window treatments and custom California Closets. Offered turnkey and fully furnished, the residence includes high-end pieces like an American Leather sofa and Westin Heavenly Bed® mattresses, along with the rare convenience of a roughed-in space for an in-unit washer and dryer. Horizons West spans 11 acres with over 300 feet of deeded beach access, a beachside pool and spa, and a serene bay-side park with a day dock. This is a rare opportunity to own a residence finished to the highest standard on the world-renowned shores of Siesta Key. Welcome home.
Listing is courtesy of: ENGEL + VOELKERS SARASOTA (941-388-9800)
Listing Agent: Brian Partie, Jr, Pa (941-544-8298)
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