Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
915 SEASIDE DR #312, Weeks 16-17, SARASOTA, FL 34242
$48,00042 Days on yellowkey MLS ID: A4692319
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1750 Built: 2009 Tax: $321 (2026)Community: Siesta Key Beach ResidencesSpa: YesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$321
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2026
Middle School: Brookside Middle
Remarks: Fractional Ownership. Experience luxury beachfront living with this Winter Fractional Package offering a 1/16th share of ownership at The Residences on Siesta Key Beach. This is a rare opportunity to own a piece of paradise on one of America’s top-rated beaches while enjoying the comfort, convenience, and services of a luxury resort. This expansive residence features a primary suite, junior primary suite, and guest bedroom, along with beautifully updated custom furnishings valued at more than $150,000. The fully equipped kitchen includes premium Wolf, Sub-Zero, and Fisher & Paykel appliances, complemented by imported linens and thoughtful details throughout. Owners enjoy legendary Hyatt Vacation Club hospitality services, including daily complimentary continental breakfast, beach service, recreation and front desk staff, assistance with local activities, valet parking, and 24-hour security. Enjoy everything you would expect from a luxury Siesta Key beachfront condominium with resort-style amenities and services, all at a fraction of the cost.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Kelly Mooney (941-587-8430)
139 S WASHINGTON DR, SARASOTA, FL 34236
$14,950,000307 Days on yellowkey MLS ID: A4661401
Bed: 5 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 7817 Built: 1936 Tax: $158,866 (2025)Community: Saint Armands Div John Ringling EstatesSpa: YesSingle Family
Taxes:$158,866
Elementary School: Southside Elementary
Tax Year: 2025
Remarks: Timeless Elegance, Effortless Living where HISTORY Meets MODERN LUXURY @ "Casa del Carnevale," an exquisite waterfront estate, situated in the prestigious St. Armands Key, the neighborhood of John Ringling Estates. This home seamlessly blends history with modern luxury, offering views of the Sarasota Waterway and Bay with a historic designation. Casa del Carnevale presents a rare opportunity to own an esteemed historical property. Offered for only the fifth time in its storied history, this exceptional estate combines Old World architectural charm with contemporary opulence. The home underwent an extensive renovation, with meticulous attention to detail and craftsmanship, utilizing top-tier materials and artisanship. Expanded from 4,000 to nearly 10,000 sq. ft. under roof, and featuring over 7,800 sq. f.t of air-conditioned space, Casa del Carnevale preserves its original charm while offering a reimagined layout that exceeds modern luxury standards. Set on three sprawling lots, 30,000+ square feet, the estate boasts 171 feet of waterfrontage, a private dock lift, a floating lift for jet skis and kayaks, and breathtaking views of Sarasota Waterway. The lush, meticulously designed tropical landscaping creates a private oasis that feels like you are walking in Selby Gardens on St. Armands. The residence includes five bedrooms and six and a half baths across two spacious levels with an elevator. Multiple terraces provide perfect outdoor retreats and entertaining areas, all complemented by stunning garden water vistas, a central courtyard, and an elegant 65' saltwater pool and spa with arched spraying fountains and iridescent glass tiles. Other luxury features include a three-car garage, elevator, nanny’s quarters, walk-in wine room, billiards room, office, and custom impact-glass arched windows designed to maximize unobstructed views. The chef’s kitchen boasts premium finishes, top-of-the-line appliances, a 5-Star La Cornue range and hood from France, featuring gas or electric ovens (kitchen art). Sub-Zero refrigerators, a Bosch dishwasher, a Miele microwave, a Miele built-in coffee machine, a stand-alone beverage refrigerator, and a stand-alone ice maker. Throughout the home, exposed beams, warm wood tones, natural stone, custom ironwork, Pecky Cypress wood throughout, and curated artwork create an inviting, sophisticated atmosphere. Offering furniture (negotiable under separate contract), and instant enjoyment to create everlasting memories, Casa del Carnevale is a rare and exquisite blend of history, elegance, and modern comfort on one of Sarasota’s most coveted waterfront estates. EASY TO SHOW. CASA DEL CARNEVALE IS A MUST-SEE IN PERSON TO FULLY APPRECIATE.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Judy Kepecz-Hays (941-587-1700)
5560 SHADOW LAWN DR, SARASOTA, FL 34242
$1,399,000508 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
Taxes:$8,052
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
$2,650,000219 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
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
$850,000152 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
$559,00054 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.
5740 MIDNIGHT PASS RD #403, SARASOTA, FL 34242
$1,950,00058 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
$1,950,000208 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)
8710 MIDNIGHT PASS RD #203B, SARASOTA, FL 34242
$699,00074 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)
1749 SANDALWOOD DR, SARASOTA, FL 34231
$2,799,000103 Days on yellowkey MLS ID: A4684519
REDUCED by $50,000 (1.8%) on 05/14/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3204 Built: 1963 Tax: $10,926 (2025)Community: Southpointe ShoresSpa: YesSingle Family
Taxes:$10,926
Elementary School: Gulf Gate Elementary
High School: Riverview High
Remarks: Tucked in the waterfront enclave of Southpointe Shores, 1749 Sandalwood Drive is a refined expression of coastal elegance and modern sophistication in a rare private compound estate in one of Sarasota’s exclusive and premier waterfront communities. Positioned just moments from the world-renowned beaches of Siesta Key, this exceptional, furnished residence offers a lifestyle defined by tranquility, beauty and effortless access to the best of Sarasota. Set beneath a canopy of mature palms and lush tropical landscaping, the home welcomes you with understated architectural grace and a sense of privacy that feels exclusive and serene. The heart of the home was thoughtfully redesigned with a complete kitchen, dining, bar and living transformation featuring Lube of Italy imported custom cabinetry, Thermador appliances including a warming drawer, Brazilian granite with semi-precious stone detailing, Italian marble flooring, and curated lighting throughout. Impact glass windows and doors enhance safety and natural light, with integrated indoor/outdoor Sonos audio, a whole-house security system with 12 cameras (2024), and dedicated electronics infrastructure providing seamless technology integration. Expansive living and entertaining areas flow seamlessly to an impressive lanai with pool and spa, creating an ideal setting for indoor-outdoor entertaining. Whether hosting sunset gatherings, enjoying a quiet morning coffee with coastal breezes, or relaxing poolside beneath the Florida sky, the home is designed to celebrate everyday living and special occasions. This home is two homes from the intercoastal. For boating enthusiasts, deepwater access provides a gateway to Sarasota Bay and beyond. A 12,000-pound boat lift and 50-amp dock service ensure convenience and capability, supporting a waterfront lifestyle, within minutes of open water and two houses from the intercoastal. Southpointe Shores is treasured for its wide canals, boating culture and established residential character. Residents enjoy proximity to premier marinas, fine dining, boutique shopping, and Sarasota’s vibrant arts and cultural scene. Siesta Key Beach, consistently ranked among the finest in the world, is just a short drive away, offering powder-soft quartz sand and breathtaking Gulf sunsets. Major updates include a new roof (2018), room addition (2018), full re-pipe (2021), pool equipment replacement (2023) and new air-conditioning systems (2024), reflecting the care and investment made throughout the years. A rare opportunity to embrace refined waterfront living in one of Sarasota’s desirable neighborhoods, where every day feels like a retreat and every evening captures the essence of coastal Florida.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Stephen Ault (513-368-8569)
2170 ROBINHOOD ST #A4-304, SARASOTA, FL 34231
$1,125,000149 Days on yellowkey MLS ID: A4677930
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1606 Built: 2026 Tax: $46,289 (2025)Community: Sarasota Bath And Racquet Club, A CondominiumCondo
Taxes:$46,289
Remarks: Under Construction. Experience refined luxury living at Bath & Racquet Residences, where modern elegance meets Sarasota’s storied legacy. This beautifully designed three-bedroom, 2.5-bath residence features floor-to-ceiling windows, custom Italian cabinetry, quartz countertops, premium Bosch appliances, and two private balconies overlooking the tranquil park setting. A separate laundry room adds to the thoughtful design and everyday convenience. Beyond your doorstep, enjoy an unparalleled collection of resort-style amenities. The community and club feature a private pool, expansive two-acre park, dog park, playground, and a scenic 1-kilometer walking trail—perfect for an active outdoor lifestyle. Sports and wellness enthusiasts will appreciate 13 tennis courts, 2 pickleball courts, 4 padel courts, a resort-style club pool, on-site restaurant, state-of-the-art fitness center, and a full-service wellness spa. Located just 4 miles from the world-famous Siesta Key beaches and 3 miles from vibrant Downtown Sarasota, this address offers the perfect blend of luxury, convenience, and coastal sophistication. Bath & Racquet Residences presents a unique opportunity for both full-time residents and investors, with short-term rentals permitted (7-night minimum), offering flexibility and income potential. Under the guidance of Tommy Haas, former World No. 2 and official club ambassador, this iconic redevelopment reimagines the historic Bath & Racquet Club, originally founded in 1969. Once the home court of tennis legends such as Chris Evert and Martina Navratilova, the property now enters a new era—honoring its rich heritage while embracing modern elegance, wellness, and active living. Designed by Halflants + Pichette Architects, Bath & Racquet Residences and Club presents 256 luxury condominiums with low HOA fees.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Cari Miller (203-722-4509)
1203 SIESTA BAYSIDE DR #1203-D, SARASOTA, FL 34242
$498,00055 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)
1249 DOCKSIDE PL #110, SARASOTA, FL 34242
$825,00080 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)
5132 JUNGLE PLUM RD, SARASOTA, FL 34242
$5,985,000396 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)
7223 CLOISTER DR #111, SARASOTA, FL 34231
$250,000216 Days on yellowkey MLS ID: C7517166
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1257 Built: 1984Monthly Fee: $525 Tax: $2,876 (2024)Community: Gulf Gate GardensCondo
Taxes:$2,876
Remarks: This thoughtfully updated and coveted corner/end unit is ready for you to call it home! A rare 2 Bedroom 2-1/2 bath townhome that boasts newer updates which include granite countertops and soft close cabinetry throughout, a stylishly designed dining room ceiling, luxury vinyl plank flooring, and an enclosed rear porch so you can enjoy the outdoors in comfort 365 days a year. Conveniently close parking and a community pool are just steps away from your door! With an abundance of shopping and restuarants in the area as well as plans for more in the old Sarasota mall location, there will be no shortage of activities. Located approximately 6 miles away from the white sands of Siesta Key beach, know that you picked a great location with all of SW Florida's prized amenities at an excellent price point! Book your showing today!
Listing is courtesy of: ERA ADVANTAGE REALTY, INC. (941-255-5300)
Listing Agent: Khari Nixon (317-503-5350)
2727 WALDEMERE ST, SARASOTA, FL 34239
$2,085,00041 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
$18,900,000137 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
$844,999121 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)
4820 KESTRAL PARK CIR #18, SARASOTA, FL 34231
$499,00023 Days on yellowkey MLS ID: A4694438
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1570 Built: 1982 Tax: $5,710 (2025)Community: Landings Carriagehouse IiCondo
Taxes:$5,710
Remarks: Welcome to one of The Landings' best-kept secrets. Tucked inside the intimate Carriage House community, this 2-bedroom, 2-bath residence delivers the feel of a single-family home wrapped in the ease of maintenance-free living ? and it's move-in ready. Inside, tile flooring flows throughout, anchoring a bright, open layout that feels larger than its footprint suggests. The updated kitchen impresses with a modern aesthetic, solid surface counters, and finishes that feel fresh and intentional, not dated. Both bathrooms have been thoughtfully remodeled, featuring solid surface counters and elegant tile enclosures. A wood-burning fireplace adds warmth and character, making this home as livable as it is lovely. Your private one-car garage sits just beyond a charming paver driveway shared with only one neighbor. This quiet, neighborly setup that feels nothing like a typical condo. Step outside and enjoy two generous lanais plus a courtyard patio designed for the kind of everyday outdoor living that makes Sarasota so irresistible. Peace of mind comes standard: a brand-new 2026 roof means this home is as solid as it is stylish. Offered unfurnished and ready for immediate occupancy. Residents of Carriage House II enjoy access to a beautiful pool and clubhouse, all set amid lush, manicured grounds surrounding a tranquil lake with fountains, turtles, and ducks. Membership to The Landings Racquet Club is available but not included or required ? a wonderful option for those who want the full lifestyle package. The Landings' coveted location west of the Trail puts everything within easy reach.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Judy Greene (941-350-0451)
3644 TIN CUP BLVD, SARASOTA, FL 34232
$450,00023 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)
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