Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
225 HOURGLASS WAY #106, SARASOTA, FL 34242
$500,000114 Days on yellowkey MLS ID: A4683200
REDUCED by $75,000 (13.0%) on 05/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1271 Built: 1969Monthly Fee: $1,566 Tax: $3,860 (2025)Community: Whispering SandsCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,860
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Step into your own island retreat with this rare ground floor END unit in the highly sought after GULF FRONT property of Whispering Sands! Perfectly positioned with a full length screened & glassed lanai overlooking the picturesque lagoon and lush tropical landscaping, this residence captures a peaceful, serene setting with a touch of everyday luxury. Thoughtfully updated and designed for effortless living, the OPEN CONCEPT floor plan features non-slip porcelain tile placed on the diagonal, skip trowel ceiling, and a spacious light-filled living space with an additional, sunny, west facing window. The nicely RENOVATED kitchen is a standout, offering granite countertops, colorful tile backsplash, a 9’ breakfast bar, white soft-close cabinetry, and a suite of GE, Whirlpool, Frigidaire, and LG appliances, all enhanced by overhead recessed, dimmable LED lighting. The cabinetry and granite extend into the entire length of the dining area, creating additional storage and an elegant serving space ideal for entertaining. The original interior living room sliders have been removed to seamlessly incorporate the lanai, transforming it into a sun-drenched sunroom that expands your cooled living space and invites the outdoors in. Just outside, a small brick paver patio off the sunroom offers the perfect spot for grilling, sunning, or unwinding after a day at the beach. Both bathrooms in this unit have been tastefully updated with NEW vanities, fixtures, and cabinetry. Additional highlights include a complete set of 2016 hurricane impact sunroom sliders and 2025 water heater. At Whispering Sands, every day feels like a vacation—with 800’ of PRIVATE beach, two heated pools with new travertine tile decks, clubhouse – currently undergoing a complete remodel which will include a catering kitchen and fitness rooms – beachside Tiki Hut, grills, and canoe/kayak—all just a short stroll to the vibrant shops and dining options of Siesta Key Village. Your island getaway awaits!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Harriet Stopher (404-316-8944)
467 CANAL RD #467, SARASOTA, FL 34242
$2,590,000578 Days on yellowkey MLS ID: A4628207
0 Days Off yellowkey (back on 5/8/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3228 Built: 2005Monthly Fee: $158 Tax: $10,222 (2023)Community: Grand Siesta 1Spa: YesTownhouse
Taxes:$10,222
Tax Year: 2023
Remarks: Under contract-accepting backup offers. Possible Seller Finance. High & Dry!! BEACH, BOATING & BISTROS!!!! SIESTA KEY`CANAL FRONT featuring WEEKLY RENTALS!! DOCK & LIFT!! GULF VIEWS!! BEACH ACCESS STEPS AWAY!!! Great location with Gulf Views steps to Public Beach Access #8 offering the ultimate waterfront lifestyle of this rare, furnished 3 bedroom/3.5 Bath plus office (or 4th bedroom), RMF-zoned opportunity on Siesta Key. Built in 2005 with high elevation and Impact Glass for peace of mind. Savor spacious living with high ceilings in 4 stories and 3,036+/- sq. ft. of living area, all accessible by stairs or private elevator, plus a ground-floor bonus room set behind the garage for your gym or office. Retreat to the large master suite, which boasts water vistas and master bath with dual vanities, granite counters, walk-in shower. Multiple terraces provide a picture-perfect panorama of your tropical setting, with each level more stunning than the last and culminating with stunning Siesta Key Beach views from the soaring top floor. Entertain with ease and style by the open, heated pool and spa, which leads to your own private dock and boatlift. Just a short boat ride on the Grand Canal to worldclass fishing and watersports. HOA is reasonably priced and lends to your comfort and convenience of maintenance-free living. Seller will also consider partial trade on storm damaged home.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Dan Miller (941-376-7442)
925 BEACH RD #107, SARASOTA, FL 34242
$568,00078 Days on yellowkey MLS ID: A4687498
REDUCED by $25,000 (4.2%) on 05/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 940 Built: 1972 Tax: $3,927 (2025)Community: La SiestaCondo
Taxes:$3,927
Remarks: Located directly across the street from world-famous Siesta Key Beach—recently ranked the #1 Beach in the United States and among the top beaches in the world— this residence offers exceptional convenience and effortless access to the sand. Simply walk to the beach in approximately five minutes—no driving, no searching for parking, just easy coastal living. Enjoy morning walks and evening sunsets on Siesta Key Beach just steps away. This 2-bedroom, 2 full bath residence offers approximately 940 square feet of comfortable living space with an open layout designed for relaxed island living. The updated kitchen features wood cabinetry, granite countertops, and stainless steel appliances, flowing seamlessly into the dining and living areas. Tile flooring throughout provides durability and easy maintenance, while the split-bedroom floor plan allows for privacy between residents and guests. One of the largest 2-bedroom, 2 full bath floor plans in the community, competitively priced at $593,000. Weekly rentals are permitted, offering outstanding flexibility for both personal use and income potential. Onsite property management is available, making guest coordination and rental operations easy and convenient. Covered parking is included, along with ample guest parking. La Siesta residents enjoy access to a heated pool, fitness room, clubhouse, and beautifully maintained grounds. Located just minutes from Siesta Key Village’s restaurants, shopping, and entertainment, this property offers the ideal balance of relaxation and accessibility. Whether you’re searching for a personal beach retreat, seasonal residence, or an income-producing investment, this location delivers the lifestyle buyers and vacationers come to Siesta Key to enjoy.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Lisa Garcia (941-266-9060)
1655 SOUTH DR, SARASOTA, FL 34239
$5,900,000104 Days on yellowkey MLS ID: A4684423
Bed: 5 Bath: 7.0 Gar: 3 Liv Area Sq Ft: 6355 Built: 2011Monthly Fee: $27 Tax: $34,625 (2025)Community: Cherokee ParkSpa: YesSingle Family
Taxes:$34,625
Elementary School: Southside Elementary
Remarks: One or more photo(s) has been virtually staged. In Sarasota's desired West of Trail enclave of Cherokee Park, 1655 South Drive, masterfully designed three-story estate where thoughtful architecture meets effortless luxury. Positioned on a homesite that is not in a Special Flood Hazard Area and enhanced with full home hurricane-impact glass and a whole-home generator, this residence offers the rare combination of refinement and peace of mind. Spanning 6,355+ square feet, the home features five bedrooms, five full baths and four half baths, with a layout tailored for grand entertaining and everyday ease. A rear three-car garage, accessed discreetly from South Lodge Drive, preserves the home's striking street presence. Inside, the main level unfolds into a wide-open living experience with a great room with wet bar, formal dining, and a showpiece chef's kitchen outfitted with Wolf dual-oven six-burner range, dual side by side 36” Sub-Zero Over-and-Under Refrigerator/Freezers, a Wolf microwave drawer, a Wolf warming drawer, and built-in Miele espresso machine. The first-floor primary suite is a private retreat, complete with an in-home gym, a spa-inspired bath and dual custom-fitted closets. A beautifully appointed guest suite (fifth bedroom) with en-suite bath also anchors the main level. Access to the upper floors is seamless via a dramatic staircase with custom wrought-iron railings or the private elevator. Upstairs, three additional en-suite bedrooms include custom walk-in closets, one thoughtfully designed with built-in bunk beds, plus a bonus club room with built-in desks and additional laundry for added convenience. Outdoors, the property transforms into a walled and gated resort-style oasis featuring a gas-heated saltwater pool with sun shelf and spa, and an artificial turf lounge/play area. A screened entertainment lounge with a convenient half pool bath connects to a full outdoor kitchen with sink, TV and gas grill, all complemented by a pergola and a mosquito misting system, ideal for Sarasota's seasons. Above the garage, a spectacular casita-style retreat, accessible by the home’s second private interior elevator or exterior spiral staircase, elevates entertaining to an entirely new level with a 2,000-bottle refrigerated wine room, a fully equipped wet bar, mini- fridge, clear ice maker, and dishwasher. Go onto the covered terrace with a gas fireplace, then unwind on the third floor in the private, pool-like infinity-edge spa, an experience that feels equal parts boutique resort and private club. Ideally in walking distance to A-rated Southside Elementary School, Southside Village, Sarasota Memorial Hospital, downtown Sarasota and short drive to the world-famous sands of Siesta Key Beach, this is a rare opportunity to own a bespoke residence in one of Sarasota's treasured neighborhoods.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Katy Mcbrayer (941-400-2406)
3415 CLARK RD #215, SARASOTA, FL 34231
$148,000210 Days on yellowkey MLS ID: A4672004
REDUCED by $1,895 (1.3%) on 05/08/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 555 Built: 1974 Tax: $2,029 (2024)Community: SiennaCondo
Taxes:$2,029
Elementary School: Gulf Gate Elementary
High School: Riverview High
Tax Year: 2024
Remarks: TOP-FLOOR END UNIT WITH WATER VIEWS! Experience the ultimate 'plug-and-play' Florida lifestyle in this charming, turnkey-furnished retreat. Perfectly positioned in a maintenance-free, two-story building, this residence overlooks a peaceful pond and is ready for immediate move-in or rental. THE TURNKEY ADVANTAGE: Sold fully furnished, including a 50” Samsung Smart TV (Living Room) and a 43” Samsung Smart TV (Bedroom). Just bring your suitcase! PEACE OF MIND: Major updates are done—New Roof (2024), Range (2025), and HVAC/Water Heater (2018). Features include a private balcony with storage, in-unit stacked washer/dryer, and a pet-friendly policy for both cats and dogs. LOCATION: Just 4 miles to Siesta Key Beach. Enjoy the heated community pool and fitness center. Whether you’re looking for a seasonal escape or a rental-ready investment, this is the best value in 34231. View the 3D Virtual Matterport Tour by clicking on the link.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Tessa Robbins, Pa (941-374-1345)
8773 MIDNIGHT PASS RD #302G, SARASOTA, FL 34242
$500,00039 Days on yellowkey MLS ID: A4691760
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1303 Built: 1981 Tax: $4,030 (2025)Community: Island Reef Ii Ph 1 2 & 3Condo
Taxes:$4,030
Remarks: Turnkey Furnished residence at Island Reef with two bedrooms and two baths. Laundry in residence. Furnished! Carport! island Reef is a serene waterfront community, one of the few gulf to Bay Community that offers many desirable amenities including: Beach, Boat Docks (lifts allowed), Two lit Tennis Courts, Pickleball, 2 Fitness Rooms, Kayak storage, Library, Billiards, Game room, Clubhouse, two Heated Pools, and Gas grills. PET FRIENDLY! Tropical Gardens add to the appeal of Island Reef and this wonderful community is close to two of Siesta Key's popular restaurants. Complimentary trolley to Siesta Beach, Siesta Village for dining, shopping, ice cream, mini donuts, cut brunch spots and dancing and live music every night of the week.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Marlene Marshall (941-539-8850)
1518 PELICAN POINT DR #257, SARASOTA, FL 34231
$537,000207 Days on yellowkey MLS ID: A4671837
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1216 Built: 1976Monthly Fee: $842 Tax: $5,556 (2024)Community: Pelican Cove IvCondo
Taxes:$5,556
Remarks: Discover one of Sarasota’s most desirable waterfront condos! It’s in great shape, with no hurricane damage. This stunning second-floor condo in Pelican Cove offers breathtaking views of Little Sarasota Bay. Imagine floor-to-ceiling glass sliders in the living room and main bedroom, along with electronic Hunter Douglas blinds, a new laundry area, and two refreshed bathrooms. Plus, you’ll have plenty of closet space and a separate, locked storage area in the carport, perfect for golf bags and at least two bikes. The kitchen has also been updated with contemporary cabinets, marble countertops, and stainless steel European Smeg appliances. The living areas feature beautiful travertine floor tiles, and the bedrooms have newer carpet. You’ll also find a new A/C system and a new hot water tank. This special home is located west of the trail but just a few minutes away, giving you easy access to all the shopping, dining, and exploring Sarasota has to offer. About Pelican Cove: It’s a lovely marina with six heated pools, a hot tub, an exercise room, tennis and pickleball courts, and clubs. You’ll love kayaking and biking here! Pelican Cove is a tropical paradise in Sarasota, a nature lover’s dream! You’ll find beautiful and expansive walking paths on exquisite grounds. Pelican Cove is also a nature conservancy and a bird sanctuary. And the view from this condo, across Little Sarasota Bay, includes a host of bird rookery islands. You can even take classes at Pelican Cove University or in yoga, tai chi, water aerobics, painting, or photography. There are over 37 clubs for photography, fiber arts, cycling, culinary arts, bridge, film, and more. Or, simply relax at the evening jazz and classical music concerts, including those held on the harbor. Located on the lush grounds of the former Wilbanks Estate, Pelican Cove is hidden away yet just minutes from everything! Come see for yourself—this is the lifestyle you deserve! Recent updates include a new refrigerator, hot water heater, laundry closet, storm and exterior door, electrical panel, and a new kitchen window.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Babette Paige (941-587-1045)
4793 OAK FOREST DR W #46, SARASOTA, FL 34231
$305,00037 Days on yellowkey MLS ID: N6144200
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1456 Built: 1984Monthly Fee: $633 Tax: $3,467 (2025)Community: Oak Forest VillasVilla
Taxes:$3,467
Remarks: One or more photo(s) has been virtually staged. Just minutes from world-famous Siesta Key, this beautifully updated maintenance-free villa offers the perfect blend of comfort, convenience, and Florida lifestyle living. Nestled in a peaceful, tree-lined community with lush mature landscaping, you’ll enjoy being close to shopping, dining, entertainment, and everything you could want in Sarasota. This spacious 2-bedroom, 2-bath residence is thoughtfully designed for both everyday living and entertaining. The bright and inviting enclosed lanai and additional living room provides flexible bonus space ideal for a home office, hobby room, formal dining area, or simply relaxing while taking in tranquil wooded views. Inside, you’ll find numerous upgrades and features, including all new flooring, an updated kitchen and new appliances in 2024 enhanced with skylights for abundant natural light, updated bathrooms, and generous walk-in closets in both the primary and guest bedrooms. Major improvements include a new paver driveway and front walkway (2024), and a new roof (2021). Additional highlights include an oversized laundry room complete with cabinetry, folding station, and utility sink, plus a 2-car attached garage. Whether you’re seeking a year-round residence or seasonal retreat, this charming villa offers low-maintenance living in an exceptional location. This fantastic community is not an age restricted community, is pet friendly and offers tennis, pickleball, heated pool and clubhouse. Schedule your private showing today and discover why this delightful community is such a wonderful place to call home. Located NOT in a flood zone and NO CDD fees.
Listing is courtesy of: CORNERSTONE R.E OF SW FL (941-404-4620)
Listing Agent: Ashley Leroy (941-724-1621)
1347 HARBOR DR, SARASOTA, FL 34239
$4,000,000138 Days on yellowkey MLS ID: A4679697
REDUCED by $300,000 (7.0%) on 05/07/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4069 Built: 2014Monthly Fee: $13 Tax: $57,247 (2025)Community: Harbor AcresSpa: YesSingle Family
Taxes:$57,247
Remarks: Exceptional Harbor Acres modern residence offering 5 bedrooms, including a sunroom converted by the owners into a true 5th bedroom (closet and A/C). Warm contemporary design with seamless indoor-outdoor living. Located in Harbor Acres, one of Sarasota’s most coveted neighborhoods, this exceptional modern residence delivers a rare blend of warm contemporary design, luxury finishes, and seamless indoor-outdoor living. Perfectly scaled for the neighborhood, the open floor plan is flooded with natural light and effortlessly blurs the line between inside and out. The great room features 8-ft pocketing sliders opening to the covered lanai, anchored by a gas fireplace with illuminated floating shelves. The chef’s kitchen is a showpiece with top-of-the-line Miele appliances, solid wood cabinetry, an expansive quartz island, LED lighting, and a butler’s pantry for effortless entertaining. A separate dining room with picturesque windows offers an inviting setting for intimate gatherings, while the adjoining family room provides a relaxed space to unwind. The first-floor primary suite is a serene retreat with walls of windows overlooking lush tropical foliage and a spa-inspired bath featuring a soaking tub and glass shower. A dedicated office/flex room is conveniently located on the main level. Owners thoughtfully converted the sunroom into a 5th bedroom, offering added flexibility for guests or multigenerational living. Sleek open-riser stairs lead upstairs to two en-suite bedrooms providing privacy and comfort.
Listing is courtesy of: MICHAELA DAMM & PARTNERS (941-726-1808)
Listing Agent: Miska Damm (941-726-1808)
6790 SARASEA CIR #6790, SARASOTA, FL 34242
$675,000211 Days on yellowkey MLS ID: A4671923
REDUCED by $44,900 (6.2%) on 04/12/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1446 Built: 1981 Tax: $5,650 (2025)Community: Midnight SeaCondo
Taxes:$5,650
Remarks: Just steps from Point of Rocks Beach! This 3BR/2.5BA townhouse with a garage at 6790 Sarasea Circle offers the best of coastal living in an exclusive 12-residence community. Enjoy direct access to Siesta Key’s world-famous beaches and village. The 1,446 sq. ft. interior features wood flooring, a cozy fireplace, and a screened lanai overlooking the pool. The bright kitchen includes white cabinetry, generous counter space, and a pass-through breakfast bar. Upstairs, 2 inviting bedrooms each feature private balconies, ample closets, and abundant natural light. Bathrooms are thoughtfully designed for comfort and convenience one on each floor, including en-suite and Jack-and-Jill layouts on the third floor. An oversized one-car garage provides direct access to a versatile lower-level bonus space, 3rd bedroom and laundry room. With up to 12 rentals allowed per year, this property offers excellent income potential in a prime island location close to dining, shopping, and downtown Sarasota.
Listing is courtesy of: GOOD LIFE REALTY LLC (941-342-9889)
Listing Agent: Raffilena Hamilton (941-685-2441)
4179 ROBERTS POINT CIR #LOT 17, SARASOTA, FL 34242
$3,400,000230 Days on yellowkey MLS ID: A4669772
Bed: 5 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 3200 Built: 2027 Tax: $5,916 (2024)Community: Roberts Point 2Spa: YesSingle Family
Taxes:$5,916
Remarks: Pre-Construction. To be built. Brought to you by Noah Thomas Builders, this newly constructed coastal residence inspired by classic West Indies architecture and situated in the exclusive Roberts Point neighborhood on Siesta Key. This thoughtfully designed home pairs timeless island style with modern coastal construction, offering refined living in a highly desirable island setting. Built to meet today’s highest coastal standards, the residence will feature solid concrete block construction, elevated foundation systems, hurricane-impact windows and doors, metal roofing, and other structural elements designed for durability and long-term peace of mind in a waterfront-adjacent environment. The interior layout emphasizes open, airy living spaces with high ceilings with abundant natural light that create an effortless connection to the outdoors. The kitchen is designed as both a functional workspace and gathering area, featuring premium appliances, custom cabinetry, and a generous island ideal for entertaining and everyday living. The primary suite serves as a private retreat with a spa-inspired bathroom, including a freestanding soaking tub, dual vanities, and a spacious walk-in shower. Additional bedrooms offer en-suite baths and refined finishes, while a flexible bonus space allows for a home office, fitness room, or lounge. Outdoor living is a focal point of the design, with covered entertaining areas, an outdoor kitchen, and a resort-style pool and spa—perfect for enjoying Siesta Key’s year-round sunshine and relaxed island atmosphere. Located on the quiet north end of Siesta Key, Roberts Point is known for its privacy, natural surroundings, and convenient proximity to Siesta Beach, Siesta Village, and downtown Sarasota. This new construction home presents a rare opportunity to experience elevated coastal living by Noah Thomas Builders in one of Sarasota’s most coveted island communities. All images, renderings, and descriptions are for illustrative purposes and represent the intended design and style by Noah Thomas Builders. Finishes, materials, and specifications are subject to change during construction. Pricing, availability, and final details may be modified prior to completion.
Listing is courtesy of: 1ST CLASS REAL ESTATE SUNCOAST (386-882-6644)
Listing Agent: Holly Wikfors, Llc (239-777-8075)
3281 BENEVA RD #104, SARASOTA, FL 34232
$199,95060 Days on yellowkey MLS ID: A4690039
REDUCED by $10,000 (4.8%) on 05/07/2026
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)
2907 MARSHALL DR, SARASOTA, FL 34239
$599,999232 Days on yellowkey MLS ID: A4669618
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1138 Built: 1954 Tax: $6,643 (2025)Community: Orange ParkSpa: YesSingle Family
Taxes:$6,643
Remarks: Investor Alert! Rare opportunity to own a turnkey income-producing property in a prime location! This fully furnished gem features a brand-new pool, all-new impact windows, and a strong rental history with future bookings already in place, cash flow from day one! Don’t miss your chance to add this high-performing asset to your portfolio. Schedule your showing today, opportunities like this don’t last!
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Inbal August (917-957-8111)
5408 EAGLES POINT CIR #302, SARASOTA, FL 34231
$339,900143 Days on yellowkey MLS ID: A4678903
REDUCED by $10,000 (2.9%) on 05/07/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1768 Built: 1990Monthly Fee: $167 Tax: $6,133 (2025)Community: Eagles Point At The Landings, Bayview Homes ISpa: NoCondo
Taxes:$6,133
Remarks: THIS IS THE LOWEST PRICE UNIT BY A STAGGERING $100,000, making it the clear standout for buyers who understand value. BRING THE OFFERS. SELLER FINANCING AVAILABLE. Discover your slice of Sarasota paradise with panoramic Intracoastal Waterway views and unforgettable sunsets from every room of this beautifully updated third-floor condo in Eagles Point at The Landings, one of Sarasota’s most desirable West of Trail, gated communities, just minutes from world-famous Siesta Key Beach and downtown. This light-filled residence showcases brand-new, top-of-the-line impact windows and an expansive triple-glass impact sliding door, offering both peace of mind and stunning views over mangroves toward Siesta Key and the Gulf beyond. The building’s common areas have also been upgraded with impact windows for added security and value. Step inside to an inviting open-concept great room, ideal for entertaining. Features include luxury vinyl plank flooring, fresh neutral paint, and designer lighting throughout. The chef’s kitchen is a standout with quartz countertops, designer tile backsplash, newer stainless steel appliances, abundant cabinetry, and an oversized island with wine and beverage refrigerator, perfect for gatherings. Double glass doors lead to the spacious primary suite, complete with a private sitting or office niche, dual walk-in closets, and a spa-inspired bath featuring double vanities and a large walk-in shower. A generously sized guest bedroom and bath are thoughtfully positioned for privacy, with gulf-facing views sure to impress visitors. The sun-drenched flex space/sunroom off the kitchen offers the home’s best view and is ideal as a breakfast café, dining nook, or serene retreat. Additional highlights include a full indoor utility room, new washer & dryer (2021), new A/C with humidistat (2021), and water heater (2020). The unit includes under-building parking, extra storage locker, kayak or paddleboard storage, bike room access, and ample guest parking. Eagles Point residents enjoy a private pool and grill area, plus membership in The Landings Racquet Club, featuring Har-Tru tennis courts, pickleball, junior Olympic lap pool, spa, fitness center, library, and an active social calendar. Enjoy a waterfront lifestyle with mangrove-lined walking paths, fishing gazebo, kayak launch on the Intracoastal, and lush tropical surroundings, all just minutes from downtown Sarasota, fine dining, shopping, and cultural attractions. Luxury, location, and lifestyle converge here. Schedule your private showing today before this opportunity is gone!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Joey Lamielle (941-350-0016)
927 CONTENTO ST, SARASOTA, FL 34242
$2,300,00048 Days on yellowkey MLS ID: A4691441
0 Days Off yellowkey (back on 4/26/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3649 Built: 2024 Tax: $13,452 (2024)Community: Siesta IslesSpa: YesSingle Family
Taxes:$13,452
Remarks: Short Sale. Partially complete. Interior is mostly complete and needs final punch-out completed and painting.
Listing is courtesy of: REALTY EXECUTIVES GALLERY (941-376-8769)
Listing Agent: Troy Jenkins (941-376-8769)
2177 SUNNYSIDE PL, SARASOTA, FL 34239
$2,650,000187 Days on yellowkey MLS ID: A4674289
REDUCED by $149,000 (5.3%) on 05/05/2026
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4624 Built: 2023 Tax: $25,349 (2024)Community: Hibiscus Park 2Spa: YesSingle Family
Taxes:$25,349
Remarks: Everything you thought you needed—and knew you wanted—now offered with an unmatched level of value and flexibility. Recently repositioned with an attractive price improvement and now offered turnkey furnished, this exceptional newer construction residence presents a rare opportunity to step into luxury living—or a high-performing rental investment—without delay. Located within the City of Sarasota limits, this home allows for weekly (7-day minimum) rentals, making it uniquely suited for those seeking both personal enjoyment and income potential. The thoughtfully curated furnishings create an immediate, seamless transition for ownership or rental readiness, blending style, comfort, and functionality throughout. Designed to elevate both lifestyle and longevity, the home features a custom ProTee golf simulator, a two-person Equinox infrared sauna, and a Renu Therapy cold plunge, offering a private wellness retreat rarely found in residential properties. Spanning over 5,400 square feet of total living space, the home showcases a clean, contemporary design with expansive glass, natural textures, and effortless indoor-outdoor flow. The resort-style outdoor setting, complete with pool, spa, and dual covered entertaining areas, pairs perfectly with the home’s open interior spaces, state-of-the-art kitchen, and dedicated home theater—creating an environment equally suited for relaxation or hosting. Positioned between Southgate, Arlington Park, and Cherokee Park, and just moments from Southside Village, this residence delivers not only luxury and location, but now an exceptional opportunity to secure a fully realized lifestyle—ready to be enjoyed from day one.
Listing Agent: Rudy Dudon (941-234-3991)
1349 GRAND BLVD #1006, SARASOTA, FL 34232
$299,000220 Days on yellowkey MLS ID: A4670997
REDUCED by $26,000 (8.0%) on 05/06/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1308 Built: 1972 Tax: $849 (2024)Community: Forest Pines 10Villa
Taxes:$849
Elementary School: Alta Vista Elementary
Remarks: Welcome to Forest Pines, a friendly 55+ community in the heart of Sarasota’s Pinecraft area. This light-filled villa offers a comfortable, open layout with tile flooring throughout and spacious bedrooms for easy living. The floor plan includes a dedicated laundry room with utility sink, covered entry and carport with extra storage, and a paver patio out back for relaxing outdoors. The primary suite features a makeup vanity and generous closet space. Added peace of mind: this property is not in a flood zone and has had no flooding during recent storms. Residents enjoy a low-maintenance lifestyle with access to community amenities and a welcoming neighborhood atmosphere. Association fees include cable TV, common area taxes, community pool, escrow reserves, lawn and grounds care, management, pool maintenance, and private road upkeep. Conveniently located just minutes from restaurants, shopping, parks, downtown Sarasota, beaches, and The Legacy Trail, this villa offers comfort, value, and an easy Florida lifestyle in one of Sarasota’s most walkable and social locations.
Listing is courtesy of: HARRY ROBBINS ASSOC INC (941-924-8346)
Listing Agent: Marlin Yoder (941-893-7406)
6146 MIDNIGHT PASS RD #12S, SARASOTA, FL 34242
$1,500,000129 Days on yellowkey MLS ID: A4680754
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1204 Built: 1967 Tax: $11,612 (2025)Community: Island HouseCondo
Taxes:$11,612
Remarks: Best beachfront value on Siesta Key!!! This second-floor condo features two bedrooms and two bathrooms, including a primary ensuite with a king-size bed and a guest bedroom. The interior offers a spacious living area, a formal dining space, and a fully equipped kitchen with granite countertops. Residents and guests can enjoy spectacular views of the Gulf of Mexico and sunsets from the private lanai. The property has recently benefited from refreshed landscaping and updated outdoor furniture. On-site amenities include a year-round heated pool, private beach access with cabanas and lounge chairs provided. A beachfront courtyard with shuffleboard, cornhole, gas grills and shaded seating are ideal for relaxation while watching sunsets. The recreation room offers air hockey, ping pong and more. Located in Island House, well known to be the top rental income producer, this unit is not only a beautiful 2nd home or vacation destination but also a highly valuable, appreciating assest/investment property. While the 2024 and 2025 seasons were impacted by hurricanes resulting in an average rental income of $80,000 a year over the last several years, these units are capable of well over $100,000. With exceptional water views and professional on-site management, this property represents a marriage of functionality, income and beauty.
Listing is courtesy of: BECKMANN REAL ESTATE (941-346-3500)
Listing Agent: Josh Beckmann (941-321-3500)
3300 BENEVA #214, SARASOTA, FL 34232
$199,999134 Days on yellowkey MLS ID: O6371947
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1084 Built: 1980 Tax: $2,279 (2025)Community: Fairways & GreensCondo
Taxes:$2,279
Remarks: ROI OPPORTUNITY – INCOME-PRODUCING PROPERTY WITH TENANT IN PLACE. Exceptional opportunity to own a 2-BEDROOM, 2-BATH condominium in the highly sought-after Fairways & Greens Condo community in Sarasota. This FIRST-FLOOR UNIT offers a bright and functional open-concept layout designed for comfortable living and effortless entertaining. The well-appointed kitchen features STAINLESS STEEL APPLIANCES and flows seamlessly into the dining and living areas, creating an inviting atmosphere filled with natural light. The spacious primary suite offers direct access to a PRIVATE ENCLOSED PATIO overlooking the COMMUNITY POOL and beautifully landscaped grounds. The second bedroom is generously sized and ideal for guests, a home office, or flexible living space. Additional highlights include a SECOND FULL BATHROOM, in-unit laundry closet with WASHER & DRYER, one ASSIGNED COVERED PARKING SPACE, and ample guest parking. TENANT-OCCUPIED WITH AN ACTIVE ONE-YEAR LEASE IN PLACE, making this a TURNKEY INVESTMENT with IMMEDIATE RENTAL INCOME from day one. Ideally located in CENTRAL SARASOTA, just 0.2 miles from Publix, 3 miles from Sarasota Memorial Hospital, and only 5.5 miles from the world-famous SIESTA KEY BEACH. Conveniently close to Arlington Park, Downtown Sarasota, Legacy Trail, premier shopping, dining, and major highways including US-41 and I-75. Perfect for investors seeking a WELL-LOCATED, INCOME-PRODUCING PROPERTY in one of Sarasota’s most desirable areas.
Listing is courtesy of: NOBSKA REAL ESTATE LLC (689-276-1593)
Listing Agent: Laura Teixeira, Pa (941-962-2413)
191 VISTA HERMOSA CIR, SARASOTA, FL 34242
$570,000128 Days on yellowkey MLS ID: A4680721
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 993 Built: 1971Monthly Fee: $1,104 Tax: $4,566 (2025)Community: Vista HermosaVilla
Taxes:$4,566
Remarks: One or more photos have been virtually staged. Welcome to your maintenance free, dream beach retreat on Siesta Key! This charming and meticulously remodeled 2-bedroom, 2-bath villa offers the perfect blend of luxury and convenience, just a short stroll from the pristine sands of Crescent Beach. Enjoy cooking in a stunning kitchen featuring brand new quartz countertops, stainless steel appliances, and stylish light fixtures. Experience comfort year-round with newly installed HVAC and energy-efficient tankless water heater. Luxury vinyl panel floors flows seamlessly throughout, offering both durability and aesthetic appeal. Relax in the attached, screened-in lanai, complete with No-See-Um screen, aluminum framing and a new Hunter, wet-rated ceiling fan, perfect for warm island evenings. Both bathrooms have been beautifully remodeled providing a fresh, contemporary feel. Located just a few steps from the Clubhouse, heated pool, outside grilling areas and laundry facility. Walking distance to shops, restaurants and entertainment. Enjoy the easy, island lifestyle with access to the free trolley service to Siesta Key Village for even more shopping and dining experiences. Ideal for a second home, rental investment, or full-time residence. Don't miss this great opportunity to own a piece of paradise! Schedule your showing today and embrace the Siesta Key lifestyle!
Listing Agent: Denise Barbato (941-400-8773)
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