Location: Sarasota
Keyword(s): Sarasota High
Keyword(s) High School: Sarasota High
Do Not Show Listings
3000 SOUTHWEST DR, SARASOTA, FL 34239
$12,750,000244 Days on yellowkey MLS ID: A4672971
REDUCED by $500,000 (3.8%) on 04/30/2026
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 8125 Built: 2003 Tax: $109,050 (2025)Community: Cherokee ParkSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$109,050
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: One of Sarasota’s greatest bayfront estates, this stunning 1.38 acre waterfront home has recently undergone a comprehensive renovation throughout, enhancing every room with refined finishes and modern systems while preserving its timeless architectural character. Hidden away at the end of Southwest Drive within the coveted Cherokee Park neighborhood, this 5-bedroom home offers exceptional seclusion and privacy, surrounded by lush, verdant landscaping, specimen trees and mature oaks, with tranquil water views providing a serene backdrop throughout the entire home. A masterpiece by design, this architectural gem was designed by esteemed architect Clifford Scholtz and built with impeccable craftsmanship by Rich Perrone of Perrone Construction. Among the recent exterior improvements are a new roof and gutters, fresh exterior paint, new decorative landscape lighting, and a refreshed outdoor shower. Inside, thoughtfully curated modern finishes and updates seamlessly blend with classic architectural details such as columns, archways, and a mahogany-paneled office, creating interiors that feel bright, open, and timeless. New European white oak flooring flows through the main living areas, while Stark carpeting adds warmth to the staircase, select bedrooms, and the bonus room. A culinary enthusiast’s dream, the completely updated kitchen boasts Taj Mahal leathered stone countertops, White Haze dolomite backsplash, a micro cement hood, painted cabinetry, an oversized island, new sinks and faucets, a Sub-Zero fridge/freezer, and more. The charming breakfast area and adjacent family room, featuring a new micro cement fireplace with Taj Mahal hearth, are set against a backdrop of expansive windows and glass doors that capture picturesque bay views. A luxurious and peaceful retreat, the elaborate primary suite features a beautifully updated bath showcasing new vanities with Taj Mahal countertops and Brizo fixtures, plus new flooring, soaking tub, and walk-in shower. Secondary baths throughout the home have also been refreshed. Covered patios and loggias extend from the main living areas, creating ideal spaces for relaxation and enjoyment. Upstairs, the expansive gathering room impresses with its custom Perla Venata quartzite bar, freshly painted ceiling beams, large windows, and balcony access overlooking the bay, pool, and lush grounds. This is the perfect perch to enjoy large gatherings, relax at the bar, shoot pool, or have friends and family over on game day. Outside, the property unfolds as a private oasis, with a screened porch featuring Chicago brick pavers, a Wolf gas grill, Sub-Zero fridge, and refreshed finishes including a tiled backsplash, updated hardware, new sink and faucet, and refinished cabinetry. Chicago brick pavers also surround the free-form pool, creating a cohesive outdoor living environment. At the water’s edge, boaters will delight in the protected deep-water boat basin with two lifts (10,000-lb. and 16,000-lb. capacities), providing effortless maritime adventures. A detached oversized 3-car garage, connected by a covered walkway, provides ample space for storage or workshop use. Additional updates of note include updated HVAC systems, tankless water heaters, and modernized electrical throughout. A whole house generator rounds out the superlative systems. This exquisitely updated estate represents a rare offering where timeless elegance meets modern sophistication on one of Sarasota's most extraordinary waterfront settings.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kim Ogilvie (941-951-6660)
160 GARDEN LN, SARASOTA, FL 34242
$4,250,000333 Days on yellowkey MLS ID: A4663247
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4086 Built: 2025 Tax: $10,687 (2024)Community: Siesta Rev Plat OfSpa: YesSingle Family
Taxes:$10,687
Elementary School: Phillippi Shores Elementary
Tax Year: 2024
Remarks: Pre-Construction. To be built. Welcome to Your Dream Coastal Retreat Steps from Siesta Beach! This custom three-story home on Siesta Key’s coveted north end features five bedrooms, 4 full and 1 half bathrooms and combines elegant design, elevated construction, and thoughtful luxury finishes. The light-filled, open-concept floor plan seamlessly connects the great room, dining space, and a gourmet chef’s kitchen, which features a quartz waterfall island, custom cabinetry, and high-end appliances. **Expansive sliding glass doors open to over 1,200 square feet of covered outdoor living space, framing views of lush tropical landscaping and a resort-style pool with a sun shelf. The primary suite is a true sanctuary, complete with a free-standing soaking tub and an oversized walk-in shower. The outdoor living experience is unrivaled. Multiple covered lanais and balconies provide perfect spaces for entertaining, relaxing with morning coffee, or enjoying Sarasota’s sunsets. **Additional features include an elevator servicing all three levels, additional guest suites, flexible bonus spaces, a two-car garage, and storm-rated windows and doors for elevated construction. Stylish coastal architecture with Hardie board siding and a metal roof completes the package. **Located just steps from Siesta Key’s world-famous beaches and minutes from the vibrant shops and restaurants of Siesta Village, this location offers the perfect blend of luxury and island lifestyle. **Short-term rentals are permitted, providing a flexible investment opportunity. **This property is also conveniently located in close proximity to Downtown Sarasota, Southside Village, and top hospitals, restaurants, and entertainment. This is your chance to build a custom masterpiece in a truly unparalleled location. Build your dream home with us, or purchase the lot and plans separately. Use our trusted general contractor or bring your own builder. Are you ready to turn your vision into a reality?
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Chad Fonder (941-961-3865)
2605 BOTANY AVE, SARASOTA, FL 34239
$555,00048 Days on yellowkey MLS ID: A4696274
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1669 Built: 1962 Tax: $2,373 (2025)Community: South Gate ManorSpa: NoSingle Family
Taxes:$2,373
Remarks: This delightful 2-bedroom, 2-bathroom home, plus space to create an office/guest house offers 1,669 square feet of inviting living space. It’s the perfect place to enjoy the laid-back Florida lifestyle. As you step inside, you’re greeted by charming terrazzo floors that bring a touch of retro style to the home. The spacious eat-in kitchen is ideal for entertaining or enjoying a quiet dinner at home. Hurricane impact windows throughout and new roof provide added storm protection, energy efficiency and peace of mind. Retreat to the primary bedroom suite that offers a comfortable and private retreat with generous closet space and an en-suite bath designed with clean finishes. Retreat outside to your private backyard oasis. The fully fenced back yard features lush gardens, creating a tranquil and picturesque setting ideal for relaxing or entertaining. The stand-alone building has been built with hurricane standards and has so many possibilities to enhance your life. Come make it your own -
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Judy Limekiller (941-374-4802)
4634 HIGEL AVE, SARASOTA, FL 34242
$6,990,00028 Days on yellowkey MLS ID: A4698367
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 3875 Built: 2024 Tax: $36,904 (2025)Community: Ocean Beach RepSpa: YesSingle Family
Taxes:$36,904
Remarks: Start living your dream lifestyle on world-famous Siesta Key in this Pham Development custom-built waterfront British West Indies–style home. Located on a quiet street on the north end of the key—close to the beach, Siesta Key Village and Out-of-Door Academy—and just minutes on and off the island, this residence offers island living at its best. Set on a corner canal-front lot, the two-story home features 5 bedrooms, 5 full bathrooms and 1 half bath, with 3,875 square feet under air, a great room floor plan, soaring 22-foot vaulted ceilings, and walls of windows and doors—including large pocket sliders—that bring in abundant natural light and seamlessly connect indoor and outdoor living. The adjacent dining area provides ample space for entertaining, while the stunning kitchen—completely open to the great room—serves as the heart of the home with a large 9-foot island with extended seating, professional stainless steel gas appliances and a walk-in butler’s pantry. The home also features a fully integrated security system, whole-home sound system and a complete Control4 smart home system. The first-floor owner’s suite offers a private retreat with a walk-in shower, freestanding tub, dual vanities, and a large custom walk-in closet. A laundry room, powder room and mudroom complete the first level, and a 3-car garage provides ample parking and storage. Upstairs you’ll find four en-suite guest bedrooms, an additional laundry area to service them, and an expansive second-level balcony to take in the views. Outdoor living includes approximately 1,502 square feet of covered lanai, an exterior wrap-around porch, and balcony space designed for enjoying the island lifestyle, complete with SunBrite outdoor TVs, and Brazilian hardwood ceilings. The privately gated driveway and fully fenced property are surrounded by lush landscaping, creating a secluded tropical setting with a large swimming pool, champagne spa and expansive pool deck perfect for relaxing or entertaining. A private well supports irrigation. With 31 linear feet of canal frontage, the property features a 31-by-12-foot electric boat lift rated for 6,500 pounds, two jet ski ramps and about a 4.5-foot draft—ideal for boating and enjoying the water, making this oasis the perfect place to enjoy the Siesta Key lifestyle.
Listing is courtesy of: PHAM REALTY GROUP LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
4117 ROBERTS POINT CIR, SARASOTA, FL 34242
$980,000516 Days on yellowkey MLS ID: A4640938
0 Days Off yellowkey (back on 6/19/2026)
Bed: 3 Bath: 2.5 Gar: 4 Liv Area Sq Ft: 2168 Built: 1990 Tax: $10,150 (2024)Community: Roberts Point 2Single Family
Taxes:$10,150
Remarks: Under contract-accepting backup offers. Nestled on a tranquil street, in the highly sought-after Roberts Point neighborhood of Siesta Key, this stunning elevated home offers the perfect blend of luxury, privacy, and coastal charm. Situated just moments from the world-renowned Siesta Beach and the vibrant Siesta Village, this beautifully maintained two-story residence offers the perfect combination of comfort, convenience, and Florida living. The layout features spacious living and dining areas, with plantation shutter windows that fill the home with natural light and allow for a seamless connection to the outdoors. The well-appointed kitchen includes modern appliances, ample cabinetry, and a large island, making it an ideal space for cooking and entertaining. The master suite is a private retreat, with plenty of closet space and an en-suite bathroom that offers a relaxing atmosphere. Additional bedrooms are generously sized and perfect for family or guests. Step outside to your private, nicely landscaped backyard, an ideal setting for relaxation and entertaining. Enjoy Florida’s beautiful weather on the expansive composite deck, complete with an outdoor shower—perfect for rinsing off after a day at the beach. The lush greenery and well-maintained yard create a tranquil, private oasis. This home’s prime location offers easy access to the best of Siesta Key—whether it's lounging on the soft sands of Siesta Beach, exploring the unique shops and restaurants in Siesta Village, or enjoying local parks and recreational activities. This is your chance to own a slice of paradise in one of the most coveted neighborhoods on Siesta Key. Schedule your private showing today and make this beautiful home your own!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Jim Mast (941-587-9066)
9161 RADIANT CIR, SARASOTA, FL 34241
$1,400,00033 Days on yellowkey MLS ID: A4697845
0 Days Off yellowkey (back on 6/28/2026)
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3847 Built: 2025Monthly Fee: $251 Tax: $6,945 (2025)Community: Cassia At Skye RanchSpa: YesSingle Family
Taxes:$6,945
Elementary School: None
Middle School: Sarasota Middle
Remarks: Experience luxury living in Skye Ranch, one of Sarasota's premier master-planned communities. Situated on a private west-facing preserve lot with no future rear neighbors, this Sand Key floor plan offers over 3,800 square feet, 5 bedrooms, 4.5 bathrooms, and an extensive list of custom upgrades.The chef's kitchen features Monogram appliances, Taj Mahal quartzite countertops with a waterfall island, and a custom wine cellar. Throughout the home, you'll find tray ceilings, 8-foot doors, luxury vinyl plank flooring throughout, no carpet anywhere in the home, designer lighting, custom window treatments, built-in Sonos speakers, and custom accent walls with fluted wood and shiplap details. The primary suite includes motorized curtains, additional sliding glass doors, a custom walk-in closet, and a spa-inspired bathroom with floor-to-ceiling tile and four shower heads. Additional highlights include a dedicated office with custom built-ins, a media room, impact windows, epoxy garage floors, and custom garage storage. Step outside to a private backyard retreat featuring a resort-style pool, panoramic screen enclosure, professional landscaping, fencing, and preserve views. Residents of Skye Ranch enjoy access to The Hub, a 25,000-square-foot amenity center with a fitness center, indoor basketball courts, rock climbing wall, café, resort-style pools, splash pads, lazy river, water slide, sports fields, parks, and more than 10 miles of walking and biking trails. A rare opportunity to own a highly upgraded pool home on a private preserve lot in one of Sarasota's most sought-after communities.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Nick Salzwedel (208-305-2923)
5780 MIDNIGHT PASS RD #407, SARASOTA, FL 34242
$1,100,00038 Days on yellowkey MLS ID: A4697559
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1361 Built: 1979 Tax: $9,178 (2025)Community: Gulf & Bay ClubSpa: YesCondo
Taxes:$9,178
Remarks: Welcome home to a fully updated, fully furnished 2 bedroom 2 bathroom beach oasis! Located in the heart of Siesta Key at the exclusive upscale Gulf & Bay Club. Featuring costal decor with modern neutral colors.This unit is nestled in B Building with direct beach access which is just steps away from your front door. Enjoy breath taking sunsets from your personal balcony or head down to the private beach for an up close view of the #1 beach in the US. The sandy white powder stretches 800 feet across this pristine 32 acre meticulously cared for tropical community. You will be impressed with world class amenities offered at Gulf & Bay Club. Enjoy the comfort of 24 hour gated security, heated pools, a fitness center, dry saunas, hot tub, tennis courts, just to name a few. Multiple barbecues and tiki hut picnic areas are great for entertaining your guests. The amenities don’t stop there, the club house has a library, bar, pool table and TV's all for your enjoyment. Not to mention the electric car charging stations and car wash on grounds. You are moments away from Siesta Village to enjoy alfresco dining with live music, specialty shopping and more! Take a short trip to the mainland and discover theater, art and fine dining. This is the island resort lifestyle you have been looking for, don't let your chance of fine beach living slip away.
Listing Agent: Sylvia Wilk (630-863-1825)
1704 FORTUNA ST, SARASOTA, FL 34239
$1,395,000100 Days on yellowkey MLS ID: A4689929
REDUCED by $80,000 (5.4%) on 06/26/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2435 Built: 2000 Tax: $12,085 (2025)Community: GranadaSingle Family
Taxes:$12,085
Remarks: Virtually Staged. Nestled on one of the most picturesque oak-lined streets in Sarasota's highly sought-after Granada neighborhood, this beautifully updated residence offers the perfect blend of elegance, privacy, and effortless Florida living. Surrounded by lush tropical landscaping and a fully fenced yard, the home lives like a maintenance-free property while providing the space, comfort, and independence of a private single-family residence. Inside, timeless finishes and thoughtful updates create a warm, inviting atmosphere. Engineered wood flooring, crown molding, plantation shutters, custom millwork, and built-in cabinetry enhance the home's sophisticated design, while fresh interior paint (May 2026), updated living room built-ins and trim (2025), and exterior landscape lighting add to its exceptional appeal. The stunning kitchen, remodeled in 2023, is designed for both everyday living and entertaining. Featuring quartz countertops, an oversized island with seating for six, and premium Sub-Zero, Thermador, and Bosch appliances—including a new cooktop (2025) and dishwasher (2024)—it flows seamlessly into the separate dining room and spacious great room with tray ceiling and custom built-ins. French doors from both living spaces open to the private pool and patio, creating the ideal indoor-outdoor lifestyle. Upstairs, three generously sized bedrooms and two full baths provide comfortable accommodations for family and guests. On the main level, a versatile den and beautifully remodeled powder bath (2023) offer the perfect space for a home office, media room, or flex living area. Step outside to your own private backyard oasis featuring a sparkling pool, mature landscaping, and multiple areas for relaxing or entertaining in complete privacy. Whether hosting friends or enjoying a quiet evening at home, this outdoor retreat is designed to embrace Florida's year-round sunshine. This home has been meticulously maintained with significant recent improvements, including two newer HVAC systems (both replaced within the last three years), a tankless water heater (2020), washer and dryer (2023), hurricane-impact windows and doors with additional hurricane shutters, a DeHart security system, and wiring and plumbing already in place for a future generator. Perfectly located just minutes from Red Rock Park, Southside Village's boutique shopping and dining, Sarasota Bay, downtown Sarasota, and the world-famous beaches of Siesta Key, this exceptional property offers the rare combination of privacy, luxury, and convenience in one of Sarasota's most desirable neighborhoods. Experience the best of Sarasota living in a home where timeless style, modern updates, and an unbeatable location come together beautifully.
Listing Agent: Kelly Baldwin (941-404-9396)
2475 BAY ST, SARASOTA, FL 34237
$2,012,000167 Days on yellowkey MLS ID: A4676732
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2874 Built: 2024 Tax: $14,004 (2025)Community: Hudson ParkSingle Family
Taxes:$14,004
Elementary School: Alta Vista Elementary
Remarks: Experience refined modern living at 2475 Bay Street, a brand-new contemporary residence offering 2,874 square feet of thoughtfully designed space. Clean architectural lines and a striking façade set the tone, while inside, sun-filled interiors reveal soaring ceilings, expansive open-concept living areas, and walls of glass that create a seamless indoor-outdoor connection. The home is designed to feel both elevated and livable, with spaces that flow naturally for entertaining, relaxing, and everyday life. The home features four bedrooms and four bathrooms, including a main-level primary suite that offers split-plan privacy and direct access to the pool area. The primary bath includes a double vanity, walk-in shower, soaking tub, and spacious his-and-hers closets with built-in accessories. The chef’s kitchen is outfitted with Café appliances accented in gold, premium cabinetry, Calcutta quartz countertops throughout the home, and a dramatic waterfall island seating eight. An upstairs living area overlooks the main level and opens to a second-story balcony, while additional bedrooms feature en-suite baths for comfort and privacy. Additional highlights include a custom resort-style pool, fully fenced yard, covered lanai with a fully equipped outdoor kitchen, two-car garage, energy-efficient construction, paver driveway accommodating up to four vehicles, and a mudroom with direct access to the pantry. Ideally located in central Sarasota, this home offers a peaceful residential setting with quick access to downtown and the area’s top attractions. Enjoy nearby Main Street dining, boutique shopping, and cultural venues such as the Sarasota Opera House, Florida Studio Theatre, and McCurdy’s Comedy Theatre. Outdoor and lifestyle destinations include Bayfront Park and Marina, Marie Selby Botanical Gardens, Payne Park, St. Armands Circle, Sarasota Jungle Gardens, The John and Mable Ringling Museum of Art, and Mote Marine Aquarium. World-renowned beaches including Siesta Key, Lido Key, and Longboat Key are just minutes away, along with convenient access to Publix, Sarasota Memorial Hospital, top schools, and Sarasota-Bradenton International Airport. Schedule your private tour and experience the design, flow, and lifestyle of this unique Sarasota property before it slips away.
Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)
Listing Agent: Desiree Doggett (941-900-6380)
2749 GREENDALE DR, SARASOTA, FL 34232
$525,00072 Days on yellowkey MLS ID: A4692947
REDUCED by $25,000 (4.5%) on 06/24/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1899 Built: 1981 Tax: $4,248 (2025)Community: Cathedral Oaks EstatesSingle Family
Taxes:$4,248
Elementary School: Brentwood Elementary
Middle School: McIntosh Middle
Remarks: Located in one of Sarasota’s best-kept secrets, Cathedral Oak Estates, this 3-bedroom, 2-bathroom home sits on a spacious 13,214 sq ft fenced lot on a quiet oak canopied cul-de-sac just a short walk to Legacy Trail. Not in a flood zone and no HOA, this centrally located property offers convenient access to downtown Sarasota, UTC, I-75, and the beaches. Lovingly maintained, the home has endless potential with room for your personal updates and design touches. The oversized driveway and 2-car garage provide plenty of space for a boat, RV, or work vehicles. Recent improvements include a new shingle roof with third nail retrofitting (2024) and sewer pipes lined (2024) with a 10-year warranty. Updated homes in the neighborhood have recently sold for approximately $365 sq ft, making this a fantastic opportunity to update and build equity.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Christina Jenkins (425-381-1917)
707 S GULFSTREAM AVE #802, SARASOTA, FL 34236
$899,000131 Days on yellowkey MLS ID: A4686314
REDUCED by $51,000 (5.4%) on 06/01/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1419 Built: 1974 Tax: $4,500 (2025)Community: Essex HouseSpa: NoCondo
Taxes:$4,500
Middle School: Booker Middle
Remarks: Experience the best of downtown Sarasota living from this beautifully renovated corner-unit condominium at 707 S. Gulfstream Avenue, ideally positioned near the bayfront, Marina Jack, Bayfront Park, Main Street, Palm Avenue, restaurants, shopping, arts, and everything downtown Sarasota has to offer. Designed for buyers seeking bayfront proximity, and easy lock-and-leave living, this move-in-ready 2-bedroom, 2-bath residence combines modern updates, everyday convenience, and peace of mind. Extensively remodeled with a fresh, sophisticated aesthetic, the condo features hurricane impact windows and doors, an open-concept layout, abundant natural light, and stylish designer finishes throughout. The oversized gourmet kitchen offers quartz countertops, premium appliances, custom cabinetry, and generous space for entertaining. The spacious primary suite includes a beautifully updated spa-inspired en-suite bath, creating a comfortable private retreat. Additional upgrades include brand-new plumbing and electrical systems. The building has also recently upgraded its generator following the 2024 storms, further adding to the value and confidence of ownership. Residents enjoy secure entry, covered parking, a resort-style pool, fitness center, and club room, all in a highly desirable downtown Sarasota location. Whether used as a full-time residence, seasonal retreat, or low-maintenance second home, this renovated Sarasota condo offers an exceptional combination of location, updates, storm protection, amenities, and lock-and-leave convenience just moments from the waterfront.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Kelly Mooney (941-587-8430)
20 WHISPERING SANDS DR #1201, SARASOTA, FL 34242
$1,195,000195 Days on yellowkey MLS ID: A4678026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1282 Built: 1973Monthly Fee: $1,398 Tax: $10,552 (2025)Community: Whispering SandsCondo
Taxes:$10,552
Remarks: A truly RARE offering, this TOP floor, GULF FRONT penthouse residence crowns the northwest CORNER of the South Tower of Whispering Sands – the premiere 55+ Gulf front enclave on the idyllic westernmost point of Siesta Key where only a fortunate few enjoy world class, panoramic views of the sparkling Gulf and 800’ of PRIVATE quartz sand beach! FULL GULF views from this unit unfurl in every direction, offering a daily masterpiece of colors that shift with the rising and setting sun. Wake up to breathtaking Gulf views that seem to stretch to infinity, offering a tranquil retreat from the ordinary. In the evening, enjoy the golden hues of Florida sunsets and starlit dinners from your expansive 28’ balcony, where the Gulf breezes and soft cries of the seagulls serve as the perfect soundtrack. This penthouse is more than just a property – it’s also a canvas for your imagination. Distinctive architectural elements and premium untapped potential invite you to curate a space that reflects your own unique style and vision. Whether you envision modern sophistication, coastal charm, or timeless elegance, the untapped possibilities of this unit invite your imagination to run free as you create the ultimate sanctuary tailored to your personal vision. Whispering Sands' relaxed, informal lifestyle provides the perfect backdrop for your next chapter. Start your day with a set of vigorous laps or water aerobics in one of two beautiful, heated pools - one beachside, one clubside. You’ll never need to leave the property to get your gym workout in the main clubhouse currently undergoing a complete remodel. Plant your feet in the cool quartz sand and enjoy daily dips in the balmy Gulf. Beach loungers are set out daily for the exclusive use of owners. Enjoy an impromptu game of beachside shuffleboard followed by a picnic supper at the Tiki Hut. Whether spending time exploring the vibrant cultural offerings of Sarasota just across the North Bridge, indulging in the local arts scene, or simply relaxing on your breezy private balcony with a good book, the options this property offers are endless. Secure your private viewing of this unique residence and claim your place in this coveted coastal community!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Harriet Stopher (404-316-8944)
105 ISLAND CIR, SARASOTA, FL 34242
$2,680,950465 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)
7714 N LEEWYNN DR, SARASOTA, FL 34240
$579,00044 Days on yellowkey MLS ID: A4696619
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2502 Built: 1973 Tax: $2,240 (2025)Community: Sarasota Golf Club Colony 3Spa: NoSingle Family
Taxes:$2,240
Elementary School: Tatum Ridge Elementary
Remarks: On more than one-third of an acre on a corner lot with no HOA restrictions, this four-bedroom, two-bath residence offers more than 2,500 square feet of living space and numerous updates. The open-concept floor plan is centered around an expansive kitchen featuring a large island with built-in storage, quartz countertops, soft-close cabinetry, a double oven with warming drawer and convection capabilities, induction cooktop, industrial-size refrigerator and a spacious pantry. Designed for everyday living and entertainment, the kitchen serves as a central gathering space within the home. Additional improvements include updated well equipment, a water softener and an indoor laundry room. Generously sized bedrooms provide comfortable accommodations. The primary en-suite boasts an updated bath with a walk-in shower and direct access to the pool area. The guest bath with access to the pool tops off the list of thoughtful improvements throughout the home, which creates a move-in-ready living experience. Outdoor living is enhanced by a resurfaced saltwater pool with a sun shelf completed in 2024, an outdoor shower and a private backyard with an invisible pet fence system. Additional features include a metal roof installed in 2018, two storage sheds and a paver front porch. The home is also equipped with solar panels through an assumable lease, offering an opportunity to benefit from renewable energy while maintaining a seamless transition for the next owner. Combining modern upgrades, extensive storage and flexible indoor-outdoor living, this property offers exceptional functionality and room to enjoy inside and out. Call today for a personal showing.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Robyn Sadlo (941-812-4219)
5005 BEE RIDGE RD, SARASOTA, FL 34233
$369,00046 Days on yellowkey MLS ID: TB8517363
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1151 Built: 1960 Tax: $3,418 (2025)Community: Ridgewood Estates 01St AddSingle Family
Taxes:$3,418
Remarks: This delightful 3-bedroom, 2-bathroom single-story home offers the perfect slice of the Florida lifestyle, boasting an established vacation rental income history for savvy buyers. Centrally located for ultimate convenience, you are a quick drive from both vibrant Downtown Sarasota and the world-famous Siesta Key Beach. You will absolutely love the expansive backyard and the peaceful view across the street. Plus, you enjoy unbeatable walkability right across the street from the 55-acre Urfer Family Park, giving you instant access to nature trails, playgrounds, and fitness paths. New roof installed in 2019, new duct work in 2020, garage door in 2015, Fuse panel was replaced in 2015! From the street, mature landscaping creates immediate curb appeal. Step inside to a bright, open-concept floor plan, controlled by a modern Google Smart Home thermostat. The chef-ready kitchen comes fully equipped with gorgeous granite countertops, a large island, and updated appliances, including a new microwave and dishwasher (both installed in 2023). Down the hall, the layout features a spacious primary suite with a dedicated workstation, a flexible second bedroom, and a comfortable third bedroom—along with a newly added washer/dryer combo (2023) for ultimate convenience. Step outside into your private backyard to find a brand-new 500+ square foot concrete patio, providing the perfect blank canvas for alfresco dining, entertaining, and soaking up the Florida sunshine. This gem comes complete with hurricane impact windows and an impact garage door installed in 2015!! Whether you are looking for a profitable investment or your own private haven, this exceptional property is a must-see!
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Krisztina Juhasz (571-423-8772)
3275 BENEVA RD #104, SARASOTA, FL 34232
$169,00071 Days on yellowkey MLS ID: A4693102
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 964 Built: 1979 Tax: $2,188 (2025)Community: Village Brooke Sec 3Spa: NoCondo
Taxes:$2,188
Elementary School: Wilkinson Elementary
Remarks: Beautifully updated 2-bedroom, 2-bath first-floor condo at 3275 Beneva Rd #104, Sarasota, FL, privately tucked away in the back of Village Brooke near the tennis courts and pool. Featuring new laminate flooring, fresh interior paint, and convenient nearby laundry facilities, this residence offers comfort, convenience, and an easy Florida lifestyle. The thoughtfully designed layout offers spacious living and dining areas filled with natural light, while the screened lanai provides the perfect place to enjoy your morning coffee or unwind in the evenings. The primary suite includes a walk-in closet and en-suite bath, creating a peaceful retreat. Village Brooke is a well-maintained community known for its lush landscaping, active amenities, and central Sarasota location close to shopping, dining, beaches, and downtown attractions. Residents enjoy multiple pools, tennis courts, shuffleboard, clubhouse activities, and beautifully maintained grounds. Whether you're searching for a year-round residence, seasonal getaway, or investment opportunity, this move-in-ready condo is a must-see. Community amenities include two heated pools, two tennis courts, a fitness center, shuffleboard, charcoal grilling areas, and scenic picnic spaces overlooking the lake and fountain. The newly renovated clubhouse features a reservable kitchen and gathering space, dining area, billiard and poker tables, ping pong, and a resident book collection — creating the perfect environment for relaxation and socializing. HOA fees include access to all amenities, water, pest control, trash, and basic cable. Short- and long-term leasing opportunities are also available (subject to association restrictions). Schedule your private showing today and discover Village Brooke Lifestyle!
Listing is courtesy of: THE AGENCY SARASOTA (941-500-5150)
Listing Agent: Sophia Kramedas-Ghanayem (302-233-0975)
1249 DOCKSIDE PL #110, SARASOTA, FL 34242
$825,000122 Days on yellowkey MLS ID: A4687526
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1217 Built: 1982 Tax: $7,705 (2025)Community: Harbour TowneCondo
Taxes:$7,705
Remarks: Welcome to your slice of paradise on Siesta Key! This beautifully maintained two-bedroom, two-bath first-floor end unit offers a blend of comfort, convenience and coastal living with no stairs to climb and easy access throughout. Ideally just a short two-block stroll to world-famous Siesta Key Beach, you’ll enjoy powdery quartz sand that stays cool underfoot, even on warmest days. This well-maintained island condominium features a roomy layout and comes fully furnished, making it move-in ready or ideal as an income-producing rental. The generous screened lanai overlooks the peaceful marina, creating a spot to relax with your morning coffee or unwind at sunset. Boating enthusiasts will appreciate the sought-after deeded boat dock, providing direct water access to the Intracoastal Waterway. The private garage with overhead storage offers plenty of extra space for beach, fishing gear and more. Within the desirable Harbour Towne community, residents enjoy a host of amenities including a heated swimming pool, spa, tennis and pickleball courts, plus a welcoming clubhouse known for its friendly, social atmosphere. Whether you're seeking a seasonal getaway or investment opportunity, this condominium checks every box. Enjoy the laid-back Siesta Key lifestyle with dining, shopping and entertainment just minutes away, all while living near one of the world’s celebrated beaches.
Listing Agent: Peg Davant (941-356-4552)
797 BEACH RD #509, SARASOTA, FL 34242
$690,000314 Days on yellowkey MLS ID: A4665033
1 Days Off yellowkey (back on 6/27/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 816 Built: 1970 Tax: $6,040 (2024)Community: Crescent RoyaleSpa: YesCondo
Taxes:$6,040
Remarks: Under contract-accepting backup offers. PENTHOUSE" OPPORTUNITY on the 5th Floor of Building 797 in Sought After & Gated CRESCENT ROYALE! As you walk through the door you will be astounded with the beautiful views of the Gulf of Mexico & Siesta Beach! Own your own piece of Siesta Key and enjoy the gorgeous nightly sunsets on the top floor. This updated unit has been well maintained and tastefully furnished, updated with a functional kitchen, updated bath and Hurricane sliding glass doors leading out to the lanai. The screened lanai will give you balmy breezes and will also provide a 180 degree view of the Gulf of Mexico. Security Gates & a beautiful paved entryway will greet you upon entering and you'll have your own, assigned covered carport space. There is plenty of guest parking available as well. There is also a storage area assigned to this unit for beach chairs, coolers, etc. on the same floor. You will be greeted with a professional and friendly staff from management to maintenance on site who handle all aspects of property management. Crescent Royale also features a new state-of-the-art fitness center, gas grills & tables with umbrellas for a cookout, shuffleboard court, Olympic style heated pool, pool table in the air conditioned lounge, elevators, recreation room & a handicap accessible banquet room with a kitchen. A short ride to siesta village with lots of shopping and nite life
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Sandy Gamble Hulvat (941-320-1964)
4205 HIGEL AVE, SARASOTA, FL 34242
$7,500,000212 Days on yellowkey MLS ID: A4675182
Bed: 4 Bath: 4.5 Gar: 12 Liv Area Sq Ft: 7003 Built: 2008Monthly Fee: $125 Tax: $60,515 (2025)Community: Cocoanut BayouSpa: YesSingle Family
Taxes:$60,515
Remarks: A timeless coastal estate with an air of refined European elegance, this gated waterfront residence on the protected deep waters of Cocoanut Bayou harmonizes classic architecture with thoughtful modern enhancements. Newly updated with wide-plank white oak engineered hardwood flooring and a gleaming white kitchen featuring new pearl quartz countertops and a Zellige tile backsplash, the home offers an elevated, move-in-ready experience for buyers seeking both luxury and serenity on Siesta Key. Step through custom arched double doors into a luminous grand foyer with 12-foot ceilings and beautifully crafted architectural details that introduce the home’s balance of scale, sophistication, and warmth. The soaring central living room, with its 24-foot ceilings, new hardwood floors, and expansive terrace, sets the tone for both intimate gatherings and grand entertaining. A sweeping 48-foot waterfront terrace extends the full width of the home, creating a captivating outdoor living space with room for dining, lounging, and enjoying breezy evenings by the stone fireplace. Inside, the newly refreshed gourmet kitchen shines with exceptional professional-grade appointments, including two Sub-Zero refrigerators, Wolf cooking equipment, two Miele dishwashers, Sub-Zero freezer drawers with ice maker, an oversized island, a casual dining area with French doors to the terrace, and an outdoor kitchen featuring a Wolf grill. The adjoining bar/butler’s pantry is well equipped with a 150-bottle, dual-temperature zoned Sub-Zero wine refrigerator and built-in Sub-Zero icemaker, along with additional glass-front cabinetry to display your treasured items. The kitchen flows effortlessly into a waterfront grand living room with five sets of French doors opening onto the terrace, for seamless indoor/outdoor living, and an elegant formal dining room for special occasions. On the opposite wing, you will find a handsome library/office, a home gym, and a large family room with serene water views and French doors to the terrace. A recently upgraded powder room and two large storage closets complete this level. The private second level, accessed by a sweeping staircase or the commercial-grade elevator, features four generous bedroom suites with walk-in closets, spa-inspired baths, and engineered hardwood flooring. The primary suite, a serene retreat, offers a gas fireplace, an expansive private terrace with bayou and bay views, the perfect spot to see incredible sunrises, and a luxurious marble bath with soaking tub, dual vanities, a large dual shower, and a built-in Sub-Zero mini-fridge. Spacious dual custom closets and a dressing area with a vanity complete the space. Boaters will appreciate the deep-water dock with direct access to Sarasota Bay and the Gulf of Mexico. Additional features include a second-floor laundry with a new Samsung washer and dryer, a 12-car garage, a whole-house sound system, impact-resistant windows and doors, concrete construction, state-of-the-art security, 4 HVAC units (one recently installed), and mature tropical landscaping that provides privacy and a true sense of retreat. A private community beach offers the rare opportunity to enjoy Siesta Key’s renowned white sands moments from home. Ideally located near Siesta Key Beach, Siesta Village, and vibrant downtown Sarasota, this exceptional estate combines architectural beauty, modern updates, and an enviable waterfront setting—offering a lifestyle entirely its own.
Listing Agent: Judie Berger (941-928-3424)
1800 WEBBER ST, SARASOTA, FL 34239
$4,490,00030 Days on yellowkey MLS ID: A4698305
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3262 Built: 2025 Tax: $12,950 (2025)Community: Poinsettia Park 2Spa: YesSingle Family
Taxes:$12,950
Remarks: Nestled in the heart of West of the Trail, this luxury single-story estate represents the pinnacle of modern living. Encompassing 3,262 square feet, the home features 4 bedrooms, 4 full bathrooms, and 2 half baths, all thoughtfully designed for both comfort and functionality. Set on an expansive 15,930-square-foot lot, the residence offers tranquility just moments from the shops and dining of Southside Village. Enjoy the convenience of a circular driveway with a custom paver design and garage space for three cars. With striking architecture, impeccable craftsmanship, and beautiful, thoughtfully curated finishings—showcasing detailed trim work and refined design throughout—this residence delivers sophistication and all-inclusive resort-style living in one of the area’s most desirable locations. Inside, soaring 18-foot vaulted ceilings and custom tray ceilings enhance the open-concept layout, while 12-foot full pocket sliders seamlessly connect indoor and outdoor living spaces. The living room is anchored by a sleek fireplace, creating a warm yet modern focal point. The chef’s kitchen is equipped with professional-grade gas appliances, a waterfall-edge quartz island, custom cabinetry, and an expansive butler’s pantry for effortless entertaining. A glass-enclosed wine display and tray ceiling details add dramatic appeal. The primary suite features 14-foot ceilings and a spa-inspired bath with a freestanding soaking tub, dual vanities, and a luxurious walk-in shower. All bedrooms include custom California Closets. A designated large office, spacious laundry room, and private gym complete the interior amenities. The home also has a full security system installed. Outdoors, the resort-style backyard showcases a heated saltwater pool and hot tub spa with elegant water features. The back patio, finished with a Brazilian hardwood ceiling, is enhanced with remote-controlled mosquito blinds with sun protection for year-round comfort, as well as a full sound system that can be app controlled. A fully equipped outdoor kitchen, fire pit, and outdoor SunBrite TV create the ultimate entertaining space, while a private putt-putt golf course adds a one-of-a-kind touch to this exceptional property. Please let us know how we can help and give us a call to set up a tour of this beautiful home. Thank you.
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