Location: Sarasota
Keyword(s): Sarasota High
Keyword(s) High School: Sarasota High
Do Not Show Listings
5560 SHADOW LAWN DR, SARASOTA, FL 34242
$1,399,000509 Days on yellowkey MLS ID: A4636955
REDUCED by $100,000 (6.7%) on 05/25/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2124 Built: 1970Monthly Fee: $17 Tax: $8,052 (2025)Community: Siesta IslesSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,052
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: One of the lowest priced homes on Siesta Key's deep boating water and only 3 blocks to the white quartz sand and aqua Gulf waters! An inviting opportunity to enjoy relaxed waterfront living on Siesta Key, this well-maintained residence is ideally positioned just minutes from the powdery white sands of world-famous Siesta Beach and the turquoise waters of the Gulf. Set on an oversized 14,000-square-foot corner lot, this four-bedroom, three-bath home blends comfortable coastal living with everyday functionality in a highly desirable island setting. Designed for effortless entertaining and easy living, the open-concept floor plan centers on a spacious island kitchen with generous seating, a breakfast bar, and abundant workspace, flowing seamlessly into the dining and living areas for gatherings both large and small. A thoughtful split-bedroom layout offers privacy for owners and guests alike. The primary suite enjoys peaceful views of the pool and canal, while a secondary bath doubles conveniently as a pool bath—ideal for indoor-outdoor living. Step outside to the covered, screened lanai and unwind beside the sparkling pool, framed by tranquil water views and gentle coastal breezes. Tucked along a quiet harbor just off the Grand Canal, the setting is ideal for kayaking, paddleboarding, or boating, with frequent sightings of manatees and coastal birds adding to the natural charm. Evenings bring glowing “mango sunsets” nearby, while mornings begin with soft sunrises reflected on the water. Additional highlights include an oversized two-car garage and a concrete tile roof. Ideally located near the shops, dining, and energy of Siesta Village—and just 15 minutes from downtown Sarasota’s vibrant arts and cultural scene—this home presents a compelling opportunity to enjoy the best of island living, whether as a full-time residence or a serene coastal retreat.
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-364-4000)
Listing Agent: Judie Berger (941-928-3424)
3512 CAMINO REAL, SARASOTA, FL 34239
$2,650,000220 Days on yellowkey MLS ID: A4671290
REDUCED by $95,000 (3.5%) on 04/21/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3810 Built: 2025 Tax: $6,583 (2025)Community: GranadaSpa: YesSingle Family
Taxes:$6,583
Elementary School: Southside Elementary
Remarks: 3512 Camino Real represents a rare opportunity to acquire a newly constructed luxury residence strategically positioned for high-performing short-term rental income in one of Sarasota’s most supply-constrained residential corridors. Located inside the City of Sarasota and approximately 10 minutes to Siesta Key Beach, Siesta Key Village, and Downtown Sarasota, this property is purpose-built to operate under a weekly rental model that aligns with current city regulations while attracting higher-quality, longer-stay guests. Unlike many coastal investment properties that rely on nightly rental volatility or regulatory gray areas, this home offers a compliant, predictable income profile paired with strong long-term appreciation fundamentals. Completed in 2025 by award-winning Heritage Builders, the British West Indies–inspired residence spans 3,810 square feet on an oversized .27-acre corner double lot, offering 5 bedrooms, 4.5 bathrooms, a dedicated office, a game room, and a 3-car garage. The layout comfortably sleeps up to 12 guests, supporting premium weekly rates and strong demand across multiple seasons. The home’s interior and exterior amenities are intentionally aligned with today’s luxury short-term rental market: a private heated resort-style pool and spa, expansive covered lanai with outdoor kitchen, open-concept living areas, high ceilings, impact-rated windows, concrete block construction, and elevated hurricane standards. These features enhance guest experience while also reducing operational risk, insurance exposure, and long-term maintenance costs—key considerations for investor underwriting. From an operational standpoint, a weekly rental strategy delivers meaningful advantages: fewer guest turnovers, lower housekeeping and wear-and-tear costs, improved booking stability, and reduced party risk. The surrounding Granada neighborhood further strengthens the investment thesis, offering oak-lined sidewalks, walkable parks, proximity to boating access, Southside Village dining, and Downtown Sarasota’s cultural and marina district—all while remaining above the flood zone, a critical differentiator for long-term ownership and asset resilience. Beyond income potential, 3512 Camino Real offers multiple exit strategies. Its new-construction pedigree, desirable residential setting, and luxury finish level support future resale to primary residents, second-home buyers, or continued investor ownership. Limited supply of large, newly built homes with pools inside Sarasota city limits underpins long-term value appreciation and broad buyer appeal across market cycles. A comprehensive Short-Term Rental Investor Report, including projected revenue, operating assumptions, conservative and upside scenarios, and long-term investment analysis, is available upon request and is attached in the MLS for qualified buyers.
Listing is courtesy of: EXP REALTY LLC (800-486-1794)
Listing Agent: Mark Coppens (941-444-0436)
1055 W PEPPERTREE DR #102AA, SARASOTA, FL 34242
$850,000153 Days on yellowkey MLS ID: A4677695
1 Days Off yellowkey (back on 5/23/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1163 Built: 1974 Tax: $4,365 (2025)Community: Peppertree Bay IvSpa: YesCondo
Taxes:$4,365
Remarks: Under contract-accepting backup offers. Rare opportunity to own one of the most resilient and desirable residences on Siesta Key! This 2-bedroom, 2-bath condominium offers 1,163 square feet of living space (1,462 gross square feet) and is ideally positioned on the west side of the building on an elevated first floor, approximately 15 feet above sea level. It is also the closest high-rise condominium to the beach, offering exceptional proximity to the Gulf. One of only six residences in the building with an expansive deck, this sought-after middle-unit location provides a truly rare outdoor living experience. The oversized deck offers ample space for dining, entertaining, or simply relaxing while enjoying coastal breezes and sunsets. The residence has demonstrated remarkable storm resilience, sustaining no damage through three major hurricanes. This is attributed to its elevated positioning, protected west-side exposure, and six hurricane-rated doors installed in 2021. Recent interior upgrades enhance both style and comfort, including luxury vinyl flooring and freshly painted walls completed in 2025. The refrigerator, washer, dryer, and garbage disposal were also replaced in 2025. A dedicated parking space conveys with the unit. Owned by the same family since 1976, the home reflects decades of pride of ownership and thoughtful care. The community features two pools and two clubhouses on both the Gulfside and Bayside, along with a Gulfside fitness center. A well-managed rental program offers flexibility for owners while preserving a relaxed residential atmosphere. Located in one of Florida’s most coveted coastal settings, this exceptional residence offers a rare blend of scarcity, storm resilience, expansive outdoor living, and resort-style amenities—making it an outstanding lifestyle choice and investment opportunity.
Listing is courtesy of: REALTY HUB (407-900-1001)
Listing Agent: Tanya Stutzman (941-504-8785)
2440 VALENCIA DR, SARASOTA, FL 34239
$559,00055 Days on yellowkey MLS ID: A4690679
REDUCED by $40,000 (6.7%) on 05/21/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1330 Built: 1956 Tax: $3,188 (2025)Community: South GateSpa: NoSingle Family
Taxes:$3,188
Remarks: Charming Sarasota home for sale with 2 bedrooms, 2 baths, over 1,300 square feet, a one-car garage, and a fully fenced backyard. Located in the highly sought-after Southside Elementary school district, this residence offers the perfect blend of charm, comfort, and convenience. Inside, beautiful terrazzo floors, integrated built-ins, and a light-filled Florida room create an inviting atmosphere with flexible space for relaxing, entertaining, or working from home. This home’s midcentury appeal and classic Florida style make it especially inviting. Ideally located near downtown Sarasota, Southside Village, Sarasota Memorial Hospital, restaurants, shopping, parks, and the beaches, this is an excellent opportunity for buyers seeking a primary residence, seasonal retreat, or investment property in Sarasota real estate, with its character, ease of living, and optimal location.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Kelly Mooney (941-587-8430)
5740 MIDNIGHT PASS RD #403, SARASOTA, FL 34242
$1,950,00059 Days on yellowkey MLS ID: A4686166
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1986 Tax: $12,418 (2025)Community: Gulf & Bay Club Ph 6Spa: YesCondo
Taxes:$12,418
Remarks: A rare and exceptional offering within Building F at Gulf & Bay Club on Siesta Key, Unit 403 presents a truly one-of-a-kind coastal retreat. Completely taken down to the studs and reimagined in 2023, this residence showcases a meticulous, high-end renovation where no detail was overlooked. From the moment you enter, you’re welcomed by a light-filled, open-concept design with sweeping direct Gulf views that immediately set the tone. The chef’s kitchen is the centerpiece of the home, anchored by a stunning 12-foot oversized island with seating for six. Featuring eco-friendly PaperStone countertops and backsplash, a full suite of premium Thermador appliances, and seamless custom finishes, the space is as functional as it is striking—all complemented by breathtaking water views as you cook and entertain. Offered turnkey furnished, the interiors are thoughtfully curated with pieces from Arhaus, Restoration Hardware, and other luxury brands, creating a cohesive and sophisticated aesthetic. The open layout flows effortlessly from kitchen to dining to living, enhanced by custom built-ins that provide both style and smart storage, including a paneled wine refrigerator. Wake up to the Gulf from your private primary suite, a serene retreat designed for both comfort and elegance. This space features a dedicated vanity area, custom walk-in closet, and a beautifully appointed en-suite bath, offering a spa-like experience within your own home. Additional highlights include engineered hardwood flooring throughout, hurricane-impact windows and sliders, solid-core doors, and extensive custom storage solutions—all contributing to the home’s elevated design and livability. This two-bedroom, two-bath residence is set within the highly sought-after Gulf & Bay Club, where residents enjoy an unmatched, resort-style lifestyle across 32 acres of lush, manicured grounds. Indulge in 800 feet of private, powdery white sand beach, three heated pools, tennis and pickleball courts, a state-of-the-art fitness center with yoga studio and saunas, and multiple clubhouses featuring lounges, billiards, and social spaces. Additional amenities include barbecue and picnic areas, freshwater lakes, and EV charging stations. Ideally located just moments from the dining, shopping, and vibrant energy of Siesta Key Village—including the iconic Sunday Drum Circle—this residence offers the perfect blend of privacy, luxury, and convenience. Unit 403 is more than a home—it’s a rare opportunity to experience the very best of Gulf-front living on Siesta Key.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Drew Jacobsen (941-253-6309)
1538 S ORANGE AVE, SARASOTA, FL 34239
$1,950,000209 Days on yellowkey MLS ID: A4672485
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2550 Built: 1954 Tax: $11,061 (2024)Community: Harbor AcresSingle Family
Taxes:$11,061
Tax Year: 2024
Remarks: This revitalized 2,550 sq' (+/-) single level home is in coveted Harbor Acres and within walking distance to the quaint Southside Village, Sarasota Bay and the energizing downtown area. Bistros, gourmet markets, art galleries and all things exciting will be yours to explore. With remodeling beginning in 2016 to Miami Dade Hurricane code regulations, improvements include the addition of a 750 sq' (+/-) Primary Suite with full bathroom for one and a 3/4 bath for another, both with walk-in closets thru-outs, modern lighting and plumbing fixtures, refurbished oak flooring, granite counters, security system, whole-house stereo speakers, new appliances, 426 sq' screened porch for outdoor entertaining, paver circular driveway with additional parking pull-outs, landscaping and dramatic lighting and a custom made art piece which is also an outdoor water feature. A new roof completed the project in 2022. The plan features a living area, separate dining room and kitchen in the center of the home, which separates the primary bedroom from the additional 2 bedrooms, for privacy. There is a storage building for outdoor accessories, a roomy 2-car, solid structure carport, water well for the sprinkler system and spray foam insulation in the attic. New HVAC, including duct work and UV light filter 2026. Not too big, not too small, no elevators, no shared parking, optional HOA dues of $125 a year and a one-of-a-kind opportunity, in a once in a lifetime location.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Nancy Mackenzie (941-330-4814)
4516 TUSCANA DR, SARASOTA, FL 34241
$1,150,00032 Days on yellowkey MLS ID: A4693430
1 Days Off yellowkey (back on 5/24/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3489 Built: 2006Monthly Fee: $169 Tax: $6,785 (2025)Community: TuscanaSpa: YesSingle Family
Taxes:$6,785
Elementary School: Lakeview Elementary
Middle School: Sarasota Middle
Remarks: Under contract-accepting backup offers. Built by renowned LEE WETHERINGTON HOMES and tucked behind the gates of the highly sought-after community of Tuscana, this exceptional residence offers the perfect blend of quality craftsmanship, timeless design, and elevated Florida living. Situated on a PREMIUM AND OVERSIZED LOT NESTLED IN A CUL-DE-SAC, surrounded by preserve and lush landscaping, the property offers exceptional privacy and peacefulness. From the moment you arrive, the home makes a striking impression with its long paver driveway, lush tropical landscaping, landscape lighting, tile roof, and stunning heavy impact-rated front doors. Freshly painted inside and out, the home has been thoughtfully updated and meticulously maintained throughout. Designed for both everyday comfort and entertaining, the spacious floor plan features 4 bedrooms, 3 bathrooms, a private den/office, and a versatile upstairs bonus room, ideal for a media room, fitness space, playroom, or additional bedroom/guest retreat. Elegant formal living and dining spaces are complemented by open-concept gathering areas filled with natural light and seamless indoor-outdoor flow through dramatic disappearing sliders. TWO BEAUTIFUL FIREPLACES anchor the main living areas, adding warmth and character to the home. At the center of the home is the gourmet kitchen featuring STUNNING NEW WHITE DOLOMITE COUNTERTOPS, natural gas cooking, paneled refrigerator, stainless appliances, custom cabinetry, oversized island seating, walk-in pantry, and reverse osmosis drinking water at kitchen sink, and an inviting breakfast area overlooking the pool and preserve through aquarium glass windows. The expansive screened lanai was designed to embrace the Florida lifestyle with multiple covered seating and entertaining spaces, outdoor kitchen, saltwater pool and spa, newer pool heater, and tranquil preserve views that create your own private outdoor oasis. The fenced backyard offers additional flexibility for pets and play, and there is a raised garden area perfect for growing vegetables, herbs, or flowers. Additional highlights include a NEW TILE ROOF completed in 11/2025, NATURAL GAS COMMUNITY, tankless water heater, newer Trane A/C in Zone 1, newer Rheem A/C in Zone 2, WHOLE-HOUSE GENERATOR powered by natural gas that also operates the air conditioning systems, WHOLE HOUSE WATER FILTRATION SYSTEM, tray and coffered ceilings, crown molding, oversized 3-car garage, and numerous quality upgrades throughout. Tuscana is an intimate gated community of only 99 homes featuring charming gas lantern-lined streets, no CDD fees, and a prime Sarasota location close to top-rated schools, golf, dining, shopping, UTC, Waterside, downtown Sarasota, and world-famous Siesta Key Beach. Rarely does a home with this combination of lot, privacy, upgrades, and location become available in Tuscana.
Listing is courtesy of: INTEGRA REALTY GROUP INC (941-527-8700)
Listing Agent: Leigh Ann Grooms (941-527-8700)
8710 MIDNIGHT PASS RD #203B, SARASOTA, FL 34242
$699,00075 Days on yellowkey MLS ID: A4688439
REDUCED by $36,000 (4.9%) on 05/05/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1650 Built: 1980 Tax: $8,179 (2025)Community: Tortuga Beach ClubSpa: YesCondo
Taxes:$8,179
Remarks: Perfect Beach Life on Siesta Key! Tortuga Beach has so much to offer. Private 77 unit complex has the small intimate feel with a luxury with it's many offerings. Private Beachfront, Tennis, Clubhouse with kitchen, library and entertainment area, indoor/outdoor community pool, sauna, sun deck with grills and seating, and boat slips across the street on the bay. There are 3 slips open for rental for $300 a year. Just fill out your application. With the friendly residents you can enjoy the relaxing atmosphere with the wonderful views of the Gulf of Mexico from daytime sunbathing to sunset pleasures. Upon arrival to the condo you will find an enclosed lanai to offer more living space in the 1650 Square feet. Kitchen has plenty of space with it's wood cabinets and granite countertops with pass through breakfast bar. New AC. Split Floor plan. Primary bedroom closet contains the washer dryer but Tortuga also offers a laundry facility if you are in need. Separate dining room just off the kitchen for entertainment. Covered Parking spot very close to the entrance and elevator for easy loading and unloading.
Listing is courtesy of: PRECISE REALTY CORP (941-400-0374)
Listing Agent: Jennifer Le Blanc (941-400-0374)
6480 MIDNIGHT PASS RD #503, SARASOTA, FL 34242
$1,199,00033 Days on yellowkey MLS ID: N6144252
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1265 Built: 1979 Tax: $9,073 (2025)Community: Siesta BreakersCondo
Taxes:$9,073
Remarks: Turnkey-furnished and move-in ready, experience the ultimate coastal lifestyle in this beautifully maintained beachfront condo located on the beautiful, world-famous Siesta Key. Enjoy the soft, white sand of Crescent beach, with a Beach Attendant managing a 200 ft section of private beach. Whether you’re searching for a full-time residence, seasonal getaway, or income-producing investment property, this luxury condo offers the perfect blend of comfort, convenience, and breathtaking Gulf views. Enjoy relaxing mornings and stunning sunsets from your private screened balcony overlooking the sparkling heated pool, tropical courtyard, and turquoise waters of the Gulf of Mexico. Inside, the condo features an open and airy floor plan filled with natural light, tile flooring throughout the main living areas, and tasteful coastal finishes. The kitchen offers ample cabinetry, stainless steel appliances, recessed lighting, tray ceiling detail, and space for entertaining guests with a breakfast bar & dining area. The spacious primary suite provides a peaceful retreat with pool view, plantation shutters and sliding doors that open to the balcony. The ensuite has been updated with dual granite vanities, large walk-in shower and abundant storage. Open the sliders to the balcony for a seamless indoor-outdoor living experience. Residents and guests enjoy resort-style amenities including a beachfront heated pool, direct private beach access with free beach lounge chairs, option to rent an umbrella or cabana, beautifully maintained grounds, covered parking, grills and lighted tennis / pickleball courts. This condo also offers excellent rental potential, making it a fantastic opportunity for investors seeking vacation rental income in one of Florida’s most desirable beach destinations. Ideally located, walk to restaurants, bars, grocery, boat/bike/kayak/jet ski rentals, gift shops and more! Wake up to the beautiful beach & ocean views, where every day feels like a vacation!
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Heather Lakeman (941-412-6083)
1203 SIESTA BAYSIDE DR #1203-D, SARASOTA, FL 34242
$498,00056 Days on yellowkey MLS ID: A4690769
REDUCED by $27,000 (5.1%) on 04/27/2026
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 959 Built: 1988 Tax: $5,340 (2025)Community: Gulf & Bay Club BaysideCondo
Taxes:$5,340
Remarks: Sellers Are Highly Motivated! Welcome to your slice of paradise on world famous Siesta Key, just steps from the powdery white sands of Siesta Beach, recently ranked the number one beach in the United States. This beautifully updated one bedroom, one bathroom residence is the perfect blend of comfort, style, and location, ideal as a primary home, vacation retreat, or income producing investment with weekly rentals allowed. From the moment you enter the gated community of Gulf and Bay Club Bayside, you are surrounded by lush tropical landscaping and a sense of pride in ownership that truly sets this community apart. This impeccably maintained residence offers easy single level living with a bright and open layout, finished in a warm neutral palette. The living and dining areas are enhanced with charming details such as wainscoting, while the updated kitchen features stainless steel appliances, beautiful countertops, and well-appointed cabinetry, all flowing seamlessly into the main living space. The oversized primary bedroom offers a peaceful retreat with a large walk-in closet, while the upgraded bathroom features a stunning tile shower, dual sinks with quartz countertops, and excellent storage. A private laundry area adds convenience, and with no carpet throughout, the home is clean, modern, and move in ready. The AC and water heater were both replaced in 2022. Enjoy your morning coffee in the adorable dining nook or unwind in the bright and airy lanai, the perfect place to relax at the end of the day. This residence also includes a rare one car garage and private driveway, making island living effortless. Gulf and Bay Club Bayside offers an exceptional array of resort style amenities including two heated pools, a clubhouse, fitness center, saunas, pickleball and tennis courts, BBQ areas, walking paths, scenic ponds with fountains, and a fishing pier on the Intracoastal Waterway where you can enjoy sunsets, dolphins, and passing boats. Private deeded beach access just across the street makes it easy to enjoy the turquoise waters and world-famous quartz sand whenever you choose. Ideally located between Siesta Key Village and Stickney Point Road, you are moments from top rated dining, boutique shopping, live entertainment, and water activities. The Siesta Key Trolley provides easy access across the island, making every day feel like a vacation. Offered furnished and thoughtfully updated, this residence truly lives larger than expected and is ready for immediate enjoyment. Whether you are looking to relax, entertain, or invest, this is an incredible opportunity to own in one of the most desirable communities on Siesta Key. Schedule your private showing today and experience the coastal lifestyle you have been dreaming of.
Listing Agent: Rachelle Golden (941-538-8998)
845 BENJAMIN FRANKLIN DR #302, SARASOTA, FL 34236
$429,00098 Days on yellowkey MLS ID: A4685441
REDUCED by $15,000 (3.4%) on 05/13/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 756 Built: 1974 Tax: $5,928 (2025)Community: Presidential TheCondo
Taxes:$5,928
Middle School: Booker Middle
Remarks: QUICK SALE NEEDED! Seller will entertain any reasonable offer. BEACH LOVERS WANTED! You can experience the Lido Key lifestyle daily in this updated 1-bedroom + den 3rd floor Condo with pool and peakaboo view of the Gulf of Mexico. Ideally located directly across from Lido Beach and a short walk to St. Armand Circle, Ted Sperling Park, and Lido Beach Park. Perfect for easy beach-to-door living!! With only 40 Units, this Boutique Community is your perfect hideaway. The property abounds with palm trees and exotic plants. There is elevator access or two sets of stairs. Recent Condo updates include custom reclaimed wood kitchen & bathroom cabinetry (from the Brooklyn Shipyard), newer appliances-stone tiled bathroom- air conditioning-hot water heater-and impact sliding doors. Being offered completely furnished (*except some artwork, antiques)- just bring your suitcases! The Bayrunner Trolley stops out front and is free. Enjoy Sarasota's extensive Arts, Restaurants and nightlife without ever worrying about parking after your day in the sun. Make an appointment to see this gem now.
Listing Agent: Wayne Fastzkie (941-315-0442)
1249 DOCKSIDE PL #110, SARASOTA, FL 34242
$825,00081 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 is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Peg Davant (941-356-4552)
5132 JUNGLE PLUM RD, SARASOTA, FL 34242
$5,985,000397 Days on yellowkey MLS ID: A4651663
Bed: 5 Bath: 6.0 Gar: 10 Liv Area Sq Ft: 6928 Built: 2008Monthly Fee: $247 Tax: $45,860 (2024)Community: Hidden HarborSpa: YesSingle Family
Taxes:$45,860
Remarks: Positioned along a deepwater canal in the private, tree-lined enclave of Hidden Harbor on Siesta Key, this remarkable estate captures the essence of timeless coastal architecture and elevated Florida living. With a design that transcends trends and nearly 7,000 square feet of thoughtfully curated interiors, the home embodies a sense of enduring sophistication, where natural materials, warm textures and elegant proportions create an atmosphere that is refined and welcoming. Just over a mile from the world-renowned sands of Siesta Key Beach, this is a home that celebrates the best of Sarasota’s lifestyle, a water connection, a celebration of indoor-outdoor living and architectural details that convey quiet luxury. Set on more than half an acre with 135 feet of water frontage, the residence opens with a stunning walnut-domed foyer, where soaring ceilings and floor-to-ceiling windows flood the space with light. Rich finishes—including Birdseye maple, tongue-and-groove cypress tray ceilings, and handcrafted millwork—are woven throughout the home, delivering a consistent sense of quality and character. The kitchen is a dream for chefs and entertainers alike, appointed with quartz countertops, a large center island, professional-grade appliances, a built-in espresso machine, and a walk-in butler’s pantry that seamlessly connects to formal and casual living areas. The owner’s suite is a private retreat, complete with a sitting room, dual walk-in closets, a spa-style bath with steam shower and a peaceful balcony overlooking the water. Each of the four guest suites offers its own en-suite bathroom and generous closet space, with three featuring walk-in closets and one boasting a built-in wall closet, ensuring privacy and comfort. Whether you need a quiet office, a vibrant game room or a cozy retreat, the bonus room, game room and loft offer the flexibility to suit your lifestyle. True to its coastal character, the home opens fully to expansive covered terraces designed for year-round enjoyment. Retractable screens, a wood-paneled ceiling, integrated fans, and ambient lighting create an outdoor living room atmosphere, complete with a fireplace and a full summer kitchen with built-in grill and bar seating. Beyond, the resort-style pool and raised spa are surrounded by tropical landscaping and natural stone decking, with multiple lounge areas designed for sun and shade. A custom fire pit anchors the space, offering a cozy, elegant setting for evening gatherings with water views. Water enthusiasts will appreciate the boat dock, built to accommodate a large vessel, complete with a boat lift. With quick access to the Intracoastal Waterway, the location is as functional as it is beautiful. Below, the expansive under-building garage offers room for more than 10 vehicles across five bays, plus a workshop, EV charging station and golf cart storage. A brand new whole-house generator was installed in June of 2025, creating peace of mind. Set on a quiet cul-de-sac just minutes from Sarasota’s best beaches, shopping, dining and cultural destinations, this rare offering is a seamless blend of timeless design, superior craftsmanship and the relaxed elegance of coastal Florida living.
Listing Agent: Joel Schemmel (941-587-4894)
2727 WALDEMERE ST, SARASOTA, FL 34239
$2,085,00042 Days on yellowkey MLS ID: A4692394
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 2809 Built: 2026 Tax: $4,732 (2025)Community: Brunks Add To City Of SarasotaSpa: YesSingle Family
Taxes:$4,732
Elementary School: Alta Vista Elementary
Remarks: Under contract-accepting backup offers. Welcome to this exceptional new construction home, ideally located in Arlington Park, one of Sarasota’s most desirable neighborhoods on a rare oversized 11,230 SqFt lot. This spacious and thoughtfully designed one-story residence offers 4 bedrooms and 4.5 bathrooms, featuring soaring ceilings and an impressive “wow” factor the moment you walk through the door. Designed for both comfort and style, the home showcases custom cabinetry, high-end finishes throughout, and a chef’s kitchen equipped with premium Thermador appliances, a walk-in pantry, and abundant storage. TVs and speaker system (indoor and outdoor) convey with the home, and additional features include built-ins and a dedicated pool bath- every detail has been carefully considered. Step outside to your private backyard retreat, complete with a sparkling saltwater pool and spa, all enclosed within a massive panoramic screen enclosure. The expansive lanai serves as a true extension of the living space, perfect for entertaining or relaxing year-round. The beautifully landscaped yard offers both privacy and curb appeal, along with ample space to park an RV or additional vehicles. Located just a short walk to Arlington Park, you’ll enjoy access to walking trails, a dog park, public swimming pool (home to the Tsunami Swim Team), as well as tennis and basketball courts. With easy access to downtown Sarasota and the area’s world-renowned beaches, this home offers the perfect blend of luxury, convenience, and lifestyle. A rare opportunity to own a truly move-in-ready home that checks every box—this one is guaranteed to impress.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Izabela Fratczak (941-525-7828)
1204 HILLVIEW DR, SARASOTA, FL 34239
$18,900,000138 Days on yellowkey MLS ID: A4677344
Bed: 6 Bath: 8.0 Gar: 3 Liv Area Sq Ft: 7687 Built: 2008 Tax: $85,253 (2025)Community: Harbor AcresSpa: NoSingle Family
Taxes:$85,253
Remarks: Set within the prestigious Harbor Acres neighborhood—one of Sarasota’s most sought-after waterfront enclaves, this stunningly renovated gated estate occupies an exceptional lot on the Hillview Point with 171 feet of Sarasota Bay frontage and sweeping, unobstructed panoramic views. This magnificent two-story residence, designed by renowned architect Cliff Scholz, offers six bedrooms, seven full baths, and two half baths, complemented by an oversized three-car garage—providing a seamless blend of architectural grandeur and everyday livability. A dramatic two-story foyer welcomes you inside, where expansive west-facing walls of glass capture breathtaking water vistas and bathe the home in natural light. The main level is thoughtfully designed for both refined entertaining and comfortable living, featuring a waterfront living room, an inviting family room, and an elegant dining room. At the heart of the home, the gourmet kitchen showcases authentic zebrawood cabinetry celebrated for its exotic grain patterns and rich natural character, paired with Quartz countertops, a generous center island, premium appliances, and a breakfast area with a dedicated coffee bar—perfectly suited for intimate mornings or hosting on a grand scale. Additional highlights include a private library, executive office, a full-service bar, and secondary laundry room. The owner’s suite is a serene waterfront sanctuary, offering tranquil Sarasota Bay views, dual spa-inspired bathrooms, three walk-in closets, and a private laundry—creating a truly elevated retreat experience. Ascend the sweeping staircase or take the private elevator to the second level, where five beautifully appointed guest suites provide exceptional comfort and privacy. Two of these suites, along with the upstairs library, enjoy coveted waterfront positioning and direct access to a spectacular 35-foot terrace overlooking Sarasota Bay—an ideal setting for morning coffee, sunset cocktails, or quiet moments of reflection. An additional laundry room on this level adds to the home’s thoughtful functionality. Outdoor living is equally impressive. Host unforgettable gatherings on the expansive 76-foot elevated terrace with summer kitchen or unwind poolside at the resort-style terrace featuring a 55-foot heated pool and generous lounging areas. For boating enthusiasts, private dockage delivers effortless access to Sarasota Bay and the open waters beyond. This extraordinary waterfront estate embodies the very essence of Sarasota luxury—where timeless design, exceptional craftsmanship, and unparalleled coastal views come together in a truly rare offering.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Stephanie Church (941-724-5448)
2639 BOUGAINVILLEA ST, SARASOTA, FL 34239
$844,999122 Days on yellowkey MLS ID: A4681333
REDUCED by $19,001 (2.2%) on 04/23/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2435 Built: 1960Monthly Fee: $17 Tax: $8,234 (2025)Community: South GateSpa: NoSingle Family
Taxes:$8,234
Remarks: Under contract-accepting backup offers. Enjoy life to the fullest in this 3 bedroom, 3 bath mid-century modern style ranch home, nestled on a near 1/3 acre lot in the sought-after South Gate neighborhood, offering over 2,400 square feet of architecturally updated and meticulously maintained living space. From the moment you arrive, this private sanctuary impresses with iconic palm trees, a custom circular paver driveway, professionally lit landscaping, and a vivid one-of-a-kind patio with a colorful front entry. Inside, the light and bright open-concept floorplan showcases flawless terrazzo flooring and a striking modern contrasted kitchen with stainless steel appliances and a large island with bar-top seating. The kitchen and living areas flow seamlessly into the family and dining room, providing ample gathering space and an entertainment center ready for modern electronics. French doors lead to an almost 40-foot screened lanai overlooking a professionally manicured, fenced, and irrigated backyard accented with coping. The primary bedroom features a private exterior entrance, space for a desk or seating area, and an en-suite bath with a walk-in closet with built-in shelving and safe, a wall-to-wall glass shower with multiple massage jets and bench seating, and a separate water closet. Two additional contemporary bedrooms and bathrooms are located on the opposite side of the home. The remodeled two-car garage is climate controlled and includes a full laundry room with utility sink. Major upgrades and systems include a standing seam metal roof, hurricane-rated impact windows and garage door, tankless water heater, whole-home generator, updated electrical system with new controls, and a plumbing system rerouted with exterior clean-outs for easy access. The home includes both a 100-gallon and 500-gallon propane tank, with the generator operating from the 500-gallon tank and the water heater capable of running from either tank, all serviced on a regular basis. Indoor comfort is enhanced by a professionally maintained HVAC system with in-duct air purification, including UV lighting and a whole-home purification system. Smart-home features allow remote control of the irrigation system, HVAC, alarm system, front door lock, and security cameras. The driveway has been recently resealed, and exterior security lighting surrounds the home. Optional membership to the South Gate Community Association offers social activities and pool access at the historic community center for a nominal fee. Ideally located just minutes to golf courses, boat clubs, Downtown Sarasota dining, shopping, nightlife, cultural events, and the world-famous beaches of Siesta Key.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Alan Macloughlin (941-780-8628)
51 S ADAMS DR, SARASOTA, FL 34236
$4,500,00024 Days on yellowkey MLS ID: A4694522
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3800 Built: 2027 Tax: $13,737 (2025)Community: Saint Armands Div John Ringling EstatesSpa: YesSingle Family
Taxes:$13,737
Remarks: Pre-Construction. To be built. Brought to you by Noah Thomas Builders, introducing an exceptional modern coastal residence, ideally located just moments from St. Armands Circle and Lido Beach. This striking home blends timeless architecture with relaxed coastal elegance, offering a refined lifestyle in one of Sarasota’s most coveted neighborhoods. Thoughtfully crafted for both everyday comfort and upscale entertaining, the residence showcases expansive light-filled interiors, soaring ceilings, and dramatic walls of impact glass that seamlessly connect indoor and outdoor living. At the heart of the home, the gourmet kitchen features an oversized island, custom cabinetry, designer finishes, and a premium appliance package tailored for effortless hosting. The well-appointed floor plan includes spacious guest suites, a private office, elevator access, and a luxurious primary retreat complete with spa-inspired amenities and oversized walk-in closets. Outdoor spaces are equally inviting, featuring covered lounge areas, a resort-style pool and spa, and lush tropical landscaping designed to create a private coastal oasis. Built to elevated FEMA-compliant standards with reinforced structural components and impact-rated windows and doors, the home was designed with durability, storm resilience, and peace of mind in mind — all while maintaining a bold architectural presence.. Spend your mornings walking the shoreline of Lido Beach, afternoons enjoying boutique shopping and waterfront dining at St. Armands Circle, and evenings relaxing in your own resort-style outdoor living space. With its timeless modern design, low-maintenance luxury lifestyle, and premier Sarasota location, this home is perfectly suited for full-time living or as an upscale seasonal getaway along Florida’s Gulf Coast.
Listing is courtesy of: 1ST CLASS REAL ESTATE SUNCOAST (386-882-6644)
Listing Agent: Holly Wikfors, Llc (239-777-8075)
3644 TIN CUP BLVD, SARASOTA, FL 34232
$450,00024 Days on yellowkey MLS ID: A4694311
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1837 Built: 2016Monthly Fee: $345 Tax: $2,939 (2025)Community: Enclave At Forest LakesTownhouse
Taxes:$2,939
Elementary School: Wilkinson Elementary
Remarks: Welcome to 3644 Tin Cup Blvd, nestled in the heart of beautiful Sarasota! This impeccably maintained 3-bedroom, 2.5-bath townhome offers the perfect blend of comfort, style, and low-maintenance Florida living. Step inside to a bright and inviting open-concept floor plan featuring tasteful upgrades and charming designer touches throughout. The spacious first-floor primary suite provides both privacy and convenience, creating an ideal retreat at the end of the day. Just beyond the living area, the extended lanai offers the perfect space to relax or entertain while overlooking peaceful green space — ideal for pets and outdoor enjoyment. This is an upgraded feature from the builder. Upstairs, you’ll find a versatile loft area, two additional bedrooms, and a bonus room currently used for storage or office space. With the addition of air conditioning, this flexible area could easily become a fourth bedroom. The attached two-car garage is equipped with a generator outlet, providing added convenience and peace of mind. Located within the exclusive gated community of Enclave, residents enjoy access to exceptional amenities including a resort-style heated pool- great for year round swimming, an outdoor gathering area with a grill, and a dog park. Just minutes from two public golf courses and with direct access to the Legacy Trail, this location offers the perfect balance of recreation, relaxation, and an active lifestyle. Fresh interior paint and evident pride of ownership make this home truly move-in ready. Ideally situated just minutes from Sarasota’s world-renowned beaches, shopping, dining, and easy interstate access, this property offers the best of Florida living. Don’t miss this incredible opportunity — schedule your private showing today before it’s gone!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Carolyn Carino, Llc (941-374-8522)
1525 MALLARD LN, SARASOTA, FL 34239
$8,250,00032 Days on yellowkey MLS ID: A4692537
Bed: 5 Bath: 5.5 Gar: 6 Liv Area Sq Ft: 5664 Built: 2021 Tax: $67,285 (2025)Community: Paradise ShoresSpa: YesSingle Family
Taxes:$67,285
Remarks: A true masterpiece of modern coastal design, this custom-built 2021 waterfront estate is a stunning showcase of luxury, craftsmanship, and breathtaking views. Nestled in the highly coveted West of Trail Paradise Shores community, this 5,664 sq. ft. architectural beauty offers five bedrooms, five and a half baths, and state-of-the-art amenities designed for the discerning buyer. Step through the custom 10-foot decorative glass entry doors, and you’re welcomed by an ambiance of refined elegance. The home’s open-concept design is accentuated by vaulted ceiling details, a showcase electric fireplace, and a multitude of custom built-ins. Hardwood flooring flows throughout the first floor and continues onto the upstairs balcony and bonus room, creating a warm yet sophisticated atmosphere. A Control4 automation system provides whole-home automation, allowing effortless control of lighting, sound, and security. At the heart of the home, the chef’s kitchen boasts top-tier Wolf and Sub-Zero appliances, including a 36” Wolf cooktop, built-in ovens, a Sub-Zero refrigerator/freezer, wine cooler, and walk-in pantry, ensuring every culinary experience is extraordinary. The built-in dining buffet/bar adds an element of effortless entertaining. The main floor primary suite is a private retreat featuring dual vanities, an oversized walk-in shower, a soaking tub, two custom-designed walk-in closets, and stunning custom ceiling details. A private en-suite guest quarter located on the first floor, offers a den and an exclusive balcony, making it a perfect sanctuary for visitors. Upstairs, three beautiful and spacious en-suite bedrooms offer privacy and comfort, while a bonus movie room provides the ultimate entertainment escape, complete with a dry bar for added convenience. Designed for seamless indoor-outdoor living, the 1,000 sq. ft. raised outdoor area is nothing short of spectacular, with the pool and spa elevated to the main living level which is at 14 feet. Lounge in the resort-style pool and spa, gather around the double-sided fireplace topped with two televisions, or enjoy dining in the fully equipped outdoor kitchen, complete with a Sub-Zero refrigerator, ice maker, and Wolf natural gas grill with side burner. Remote-controlled retractable screens offer sun/shade versatility for a comfortable outdoor retreat year-round, while the fire bowls and lush landscaping create an enchanting ambiance. For boating enthusiasts, this estate boasts 123 feet of seawall and water frontage, a private dock, a 20,000 lb boat lift, and two jet ski lifts, offering direct access to the Gulf of Mexico – no bridges, just open water. Engineered for both beauty and resilience, the home sits at an elevation of 14 feet, with PGT high impact security windows and doors, spray foam insulation, a concrete tile roof, and a whole-house Kohler generator. An elevator services all three levels, leading to the sky deck, where panoramic views of Sarasota Bay and downtown create an remarkable backdrop. The 6 plus car garage with epoxy flooring provides ample space for a car collection and additional storage. Located just a short walk to Southside Village, you’ll enjoy some of Sarasota’s finest dining and boutique shopping, including Morton’s, Libby’s, and Veronica’s. With downtown Sarasota and Siesta Beach just a quick drive away, this home offers the ultimate combination of luxury, lifestyle, and location. Experience unparalleled waterfront living—schedule your private showing today.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Robert Ruiz (941-544-3299)
3118 KEY WAY, SARASOTA, FL 34239
$599,000101 Days on yellowkey MLS ID: A4685119
0 Days Off yellowkey (back on 5/22/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2370 Built: 1961 Tax: $2,942 (2025)Community: SouthgateSpa: NoSingle Family
Taxes:$2,942
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Beautifully updated 4-bedroom, 2-bath pool home in the desirable Southgate neighborhood of Sarasota offering the ideal blend of indoor comfort and outdoor Florida living. The home features a bright open layout with expansive pocket sliding glass doors that fully open to an oversized open-air pool and patio, perfect for entertaining and relaxing. The updated kitchen includes extensive custom cabinetry with built-in pantry storage and a discreetly integrated laundry area. The home offers four spacious bedrooms and two bathrooms, including a guest bath with a soaking tub. Outside, the property features a large additional paved parking pad along with the driveway and garage, providing ample space for multiple vehicles and recreational equipment. With minimal deed restrictions, the property allows RV and boat parking, with additional space along the side of the home. The backyard also includes a custom playground area. Conveniently located just minutes from Siesta Key Beach, downtown Sarasota, shopping, dining, and parks.
Listing is courtesy of: PREMIER AGENT NETWORK (877-663-9366)
Listing Agent: Stephanie Hawkins (941-587-4337)
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