Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
915 SEASIDE DR #611, SARASOTA, FL 34242
$2,950,000Listed 06/19/2026 12:27PM MLS ID: A4697522
Bed: 4 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 2625 Built: 2009 Tax: $33,482 (2025)Community: Siesta Key Beach Residences IiSpa: YesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$33,482
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Experience elevated Gulf-front living from the 6th floor of this exceptional four-bedroom, four-bath residence at The Residences on Siesta Key Beach. Perfectly positioned to capture breathtaking, unobstructed views of the Gulf of Mexico, this luxury condominium offers a front-row seat to Sarasota's legendary sunsets, the soothing sounds of the waves, and the ultimate beachfront lifestyle. Spanning more than 2,600 square feet, the thoughtfully designed interior blends sophisticated coastal elegance with effortless comfort. High-end finishes, designer furnishings, premium appliances, spa-inspired baths, and an expansive open-concept floor plan create an ideal setting for both everyday living and entertaining. What truly sets this residence apart is the unparalleled ownership experience. Residents enjoy exclusive access to the world-class amenities and services associated with the neighboring Hyatt Residence Club, including concierge services, a beachfront pool and spa, valet parking, an owners' lounge, daily breakfast service, fitness facilities, towel and chair service, and attentive resort-style hospitality. For those seeking flexibility and income potential, the property benefits from an established onsite management and rental program, making ownership as effortless as it is rewarding. Whether enjoyed as a primary residence, seasonal retreat, or luxury investment property, this residence offers a rare opportunity to combine personal enjoyment with strong rental appeal. Located on the highly sought-after south end of Siesta Key, you're just moments from waterfront dining, shopping, entertainment, the marina, and all the charm of island living, while still enjoying a private beachfront setting. Offered turnkey furnished, this is a seamless opportunity to step into one of Siesta Key's most prestigious Gulf-front addresses and begin enjoying the luxury resort lifestyle.
Listing is courtesy of: THE SARASOTA REAL ESTATE COMP. (941-321-5595)
Listing Agent: David Lehrman (941-321-5595)
2429 WHIPPOORWILL CIR, SARASOTA, FL 34231
$740,000183 Days on yellowkey MLS ID: A4675587
REDUCED by $9,999 (1.3%) on 06/19/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3002 Built: 1991 Tax: $7,729 (2025)Community: Weslo WillowsSpa: NoSingle Family
Taxes:$7,729
High School: Riverview High
Remarks: This MULTI-GENERATIONAL home has a total of four bedrooms with Two Primary Suites located on both the 1st and 2nd floors. Two additional upstairs bedrooms share a full bath with a tub. The ample Foyer with Cathedral Ceilings leads to the Open Living & Dining area; and the 15’ x 21’ Family Room with fireplace. A Den with murphy bed and a half bath are adjacent to Foyer. The enclosed porch opens to a covered patio and a spiral staircase leading to the roof deck above the first-floor Primary. Seller offering credit of up to $10,000 towards repairs & improvements. The hot tub is ready, and the laundry room plus 3-car garage offer ample storage. Repairs to roof deck surface to be scheduled for July. This home is conveniently located to the beaches, schools, shopping, and downtown Sarasota.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Sandra Walker (941-400-5849)
4660 OCEAN BLVD #Q2, SARASOTA, FL 34242
$624,90049 Days on yellowkey MLS ID: A4692194
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1200 Built: 1971 Tax: $6,131 (2025)Community: Sea VillageSpa: NoCondo
Taxes:$6,131
Remarks: BEST PRICED GULF-FRONT CONDO ON SIESTA KEY, in terms of VIEW, CONDITION, SIZE, AMENITIES and PROXIMITY to Siesta Key Village, the #1 BEACH IN America, and DOWNTOWN SARASOTA! Not ONE, but TWO heated GULF FRONT POOLS. Brand NEW fishing dock. This lovely unit can come partially furnished if you wish (a full list of items is available) and has a BRAND-NEW A/C. MOVE IN READY! Unobstructed GULF VIEWS, forever YOURS! And it’s PET FRIENDLY! HOA covers just about everything! Bring your suitcase, your toothbrush and your bathing suit! Wake up to breathtaking Gulf views, watch as dolphins swim, and enjoy legendary Siesta Key sunsets from this beautifully maintained 2-bed, 2-bath, perfectly positioned condo in a charming Gulf front community. Floor-to-ceiling glass sliders flood the open living area and primary bedroom with natural light, leading to your private screened lanai, where uninterrupted Gulf views are yours to behold. The primary bedroom features ample closet space and an ensuite bath with separate vanity. With 1,200 ft² of living space, this second-floor residence comes with an in-unit washer/dryer, as well as a free community laundry room and storage. The second bedroom is perfect for guests and family, and the well-appointed kitchen has upgraded appliances and a pass-through to the living area. This exceptional unit has had just one owner and has been in the family since the complex was built. Sea Village is a small community located exactly 1 mile north of Siesta Key Village and 1 mile to the #1 Beach in America. Amenities include two heated gulf front pools, a newly constructed fishing pier, and designated covered parking. ALL assessments have been PAID. Monthly HOA covers Community Pool, Escrow Reserves, Insurance, Exterior Maintenance (to include the roof), Maintenance of the Grounds, as well as Water, Sewer and Trash. Renowned for its vibrant coastal lifestyle, Siesta Key Village is bustling with restaurants, cafes, shops and miles of crystalline beaches. Downtown Sarasota’s Bayfront, with its world-class shopping, dining, & cultural events is 5 miles away. Nature lovers, sports enthusiasts, and patrons of the arts have the best of Sarasota at their fingertips with outdoor activities that include waterfront dining, boating, biking, golfing, hiking & fishing nearby. With easy access to state-of-the-art medical facilities, Sarasota International Airport, and the I-75, the location of this property offers the perfect blend of serenity & convenience and offers an extraordinary opportunity to LIVE YOUR BEST LIFE, whether it be used as a private retreat for your own personal enjoyment, or a seasonal or annual rental, with excellent income potential.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Robin Leonardi (941-685-6270)
5780 MIDNIGHT PASS RD #210, SARASOTA, FL 34242
$999,000199 Days on yellowkey MLS ID: A4673708
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1361 Built: 1979 Tax: $9,269 (2025)Community: Gulf & Bay Club Ph 2Condo
Taxes:$9,269
Remarks: BEST VALUE AT SIESTA KEY BEACH GULF & BAY CLUB. Imagine living in Paradise…Welcome to your dream home on Siesta Key, where every day feels like a vacation. This beautiful beachfront corner unit in the prestigious GULF & BAY CLUB is located on the #1 Beach in America per Trip Advisor. Step into this stunning two-bedroom, two-bathroom unit, filled with natural light from expansive windows. Enjoy breathtaking sunrise and sunset views as part of your daily routine. The renovated interior features high ceilings, a gourmet kitchen with an office, modern bathrooms, smart storages and elegant details. Gulf & Bay Club is the gated resort community on the key. The serene property spans on 32 acres with 800 feet of private quartz sand beach, offering exceptional living. Beyond your home, Gulf & Bay Club offers world-class amenities, including scenic pathways to a freshwater lake with a rustic footbridge, a lush tropical courtyard with 3 heated pools, 6 pickleball courts, 4 tennis courts, 2 clubhouses and barbecue grills for social gatherings. Fitness enthusiasts can access a commercial gym, sauna, and media facility, while EV charging stations promote eco-friendliness. With an on-site rental management for one-month minimum rentals, this property is perfect for luxurious living and smart investment. Make this waterfront oasis your home where warm hospitality and serenity await.
Listing Agent: Maurice Menager (941-238-8119)
3317 PINE VALLEY DR, SARASOTA, FL 34239
$550,000292 Days on yellowkey MLS ID: A4663718
REDUCED by $15,656 (2.8%) on 06/19/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2200 Built: 1964 Tax: $4,160 (2024)Community: Frst Lakes Country Club EstatesSingle Family
Taxes:$4,160
Elementary School: Wilkinson Elementary
Tax Year: 2024
Remarks: REMODELED SPACIOUS OPEN FLOOR PLAN IN FOREST LAKES COUNTRY CLUB CLOSE TO GOLF COURSE THIS CLASSIC FEATURES A NEW KITCHEN WITH A TON OF SHAKER CABINETS AND QUARTZ COUNTER TOPS. ALL NEW STAINLESS APPLIANCES INCLUDING A KITCHENAIDE FRENCH DRAWER REFRIGERATOR.THE REMODEL INCLUDED NEW HURRICANE RATED WINDOWS THROUGHOUT AND A NEW BARREL TILE ROOF. THE INTERIOR IS FRESHLY PAINTED AND HAS ALL NEW DOORS. THE FLOORS FEATURE A MODERN WOODLIKE LAMINATE WHICH GIVES THE INTERIOR A WARM COZY FEEL. BATHROOMS WERE UPDATED WITHOUT NEW VANITIES SHOWER TILE AND STYLISH ARMITAGE AQUA FIXTURES. THE INTERIOR HAS MANY 54" CASA SALERNO CEILING FANS. HUGE FAMILY ROOM WITH FIVE PICTURES WINDOWS OVER LOOKING A SHADY BACKYARD BRINGS A TOUCH OF NATURE INSIDE.THIS EKEGANT HOME ALSO FEATURES A NEW TANKLESS HOT WATER HEATER, NEW LANDSCAPING BEDS, MYRAID OF CLOSET SPACE AND FRESHLY PAINTED EXTERIOR. THE ONLY THING MISSING IS YOU AND YOUR FRUNITURE!!
Listing is courtesy of: SUNREAL ESTATE INC (941-376-7653)
Listing Agent: Karl Helbig (941-376-7653)
5880 MIDNIGHT PASS RD #804, SARASOTA, FL 34242
$1,350,000140 Days on yellowkey MLS ID: A4680425
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1498 Built: 1982 Tax: $11,821 (2025)Community: CasarinaSpa: YesCondo
Taxes:$11,821
Remarks: An unusual price for an unusual seaside residence. Completely renovated with stunning views from every window. Enjoy your morning coffee on the lanai and relish the downtown skyline as well as the Gulf of Mexico and Siesta Beach. Renovations include completely repainted, impact resistance windows, new interior doors, closet organizers and new front door. Casarina amenities include heated pool/spa, pickle ball/tennis courts, exercise room, gas grills, etc. This is worth a visit to see everything you can bring into your life.
1035 SEASIDE DR #404, SARASOTA, FL 34242
$2,650,000211 Days on yellowkey MLS ID: A4672742
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1646 Built: 2023 Tax: $18,228 (2024)Community: Ten35 SeasideSpa: YesCondo
Taxes:$18,228
Remarks: Experience beachfront ownership that works for you. Residence 404 at Ten35 Seaside offers a rare opportunity to own a fully operational, income-producing property on Siesta Key’s Crescent Beach — one of the most sought-after vacation rental destinations in Florida. This residence is enrolled in the community’s on-site professional rental management program and is already completely booked for the current season, providing immediate revenue and eliminating the uncertainty, setup time, and operational burden typical of vacation rental ownership. Owners benefit from a true turnkey investment: marketing, guest services, housekeeping, and day-to-day management are handled on-site, allowing you to generate income while still reserving personal use. Inside, the unit is designed specifically for both durability and guest appeal. Floor-to-ceiling hurricane-rated glass fills the open living space with natural light, while porcelain wood-look flooring, custom finishes, and curated furnishings create the upscale coastal experience today’s renters actively seek and review highly. The kitchen features quartz countertops and premium Wolf appliances, opening seamlessly to the living area — ideal for group stays and longer bookings. The flexible floor plan maximizes occupancy potential, with a spacious primary suite, guest bedroom, and an integrated Italian fold-down bed system that expands sleeping capacity without sacrificing aesthetics — an important driver of rental performance. The private covered lanai captures panoramic Gulf views, a major booking advantage and one of the most requested amenities among Siesta Key vacationers. Ten35 Seaside functions as a boutique resort for guests and owners alike, offering: • Direct beach access to Crescent Beach • Gulf-front pool and spa • Private cabanas • Fitness center • Fire pit and gathering areas • Daily beach chair and umbrella service Rental parameters allow one-week minimum stays in the off-season and two-week minimums during peak season, striking an ideal balance between revenue generation and property preservation. Located moments from Siesta Key’s South Village dining and shopping, the property consistently attracts repeat visitors — a key factor in maintaining strong occupancy. Whether you are expanding a portfolio, completing a 1031 exchange, or seeking a vacation home that offsets ownership costs, Unit 404 offers a combination rarely found on Siesta Key: Gulf-front location, professional management, and immediate rental income from day one.
Listing is courtesy of: EXP REALTY LLC (800-486-1794)
Listing Agent: Jeff Lauer (941-441-6555)
1671 ARLINGTON ST, SARASOTA, FL 34239
$2,995,000106 Days on yellowkey MLS ID: A4684899
Bed: 5 Bath: 5.5 Liv Area Sq Ft: 3564 Built: 2026 Tax: $10,197 (2025)Community: Lewis Combs SubSpa: YesSingle Family
Taxes:$10,197
Elementary School: Southside Elementary
Remarks: Located West of Trail, this beautiful new construction five-bedroom, five-and-a-half-bathroom residence captures the essence of Sarasota living. Designed with both comfort and entertaining in mind, the home features expansive sliding glass doors that open the main living areas to a private pool and outdoor gathering space, creating a seamless connection between indoor and outdoor living. Inside, generous living spaces, clean architectural lines, and refined finishes create a warm yet modern atmosphere. The open-concept layout centers around a spacious kitchen and living area, ideal for everyday living while also providing an elegant setting for hosting family and friends. Upstairs, well-appointed bedroom suites give privacy and flexibility, while the primary suite provides a peaceful retreat with a spa-like bath and thoughtfully designed closet space. Every detail of the home has been carefully considered to deliver both functionality and timeless style. Thoughtfully designed for comfort and ease, the property offers a low-maintenance lifestyle that appeals to both full-time residents and seasonal owners looking for a lock-and-leave Sarasota home. Ideally located just minutes from Southside Village, downtown Sarasota, Sarasota Memorial Hospital, and the Gulf beaches, the home places you close to the best dining, shopping, and coastal experiences the area has to offer while maintaining the quiet charm that has long made West of Trail one of Sarasota’s most desirable neighborhoods.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Steven Moore (401-767-7180)
3317 BOUGAINVILLEA ST, SARASOTA, FL 34239
$445,00030 Days on yellowkey MLS ID: A4694271
REDUCED by $5,000 (1.1%) on 06/19/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1514 Built: 1962 Tax: $4,960 (2025)Community: South Gate ManorSpa: NoSingle Family
Taxes:$4,960
Remarks: Virtually Staged. Southgate Charm + Space to Dream in One of Sarasota’s Most Established Neighborhoods. Situated on an oversized lot in the sought-after South Gate community, this 3-bedroom, 2-bath home offers the kind of outdoor potential that is increasingly hard to find in Sarasota. With beautiful curb appeal and a welcoming layout featuring a sunroom, spacious living areas, and dedicated dining space, this property is ready for everyday living now with room to create something extraordinary later. The expansive backyard provides ample space for a future resort-style pool, outdoor entertaining area, or private tropical retreat. Inside, the floor plan balances functionality and flexibility with multiple gathering spaces, generous bedroom sizes, pantry storage, and a sun-filled bonus room perfect for morning coffee, hobbies, or additional living space. The oversized lot offers privacy and possibilities whether you envision lush landscaping, an outdoor kitchen, or a custom backyard oasis. Residents love the central Sarasota location with convenient access to Siesta Key Beach, downtown Sarasota, shopping, dining, medical facilities, and everyday conveniences. This is an opportunity to own in a neighborhood known for mature trees, character, and proximity to the best of Sarasota living.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Nick Salzwedel (208-305-2923)
2373 PROSPECT ST, SARASOTA, FL 34239
$1,120,0009 Days on yellowkey MLS ID: A4696568
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1917 Built: 2019 Tax: $13,907 (2025)Community: Loma Linda ParkSpa: NoSingle Family
Taxes:$13,907
Elementary School: Alta Vista Elementary
Remarks: CUSTOM-BUILT by Milano Homes in 2019, this CONTEMPORARY POOL HOME combines modern design, exceptional construction, and an unbeatable Arlington Park location. Situated on a private corner lot just blocks from Sarasota Memorial Hospital and minutes to Downtown Sarasota, Southside Village, Bayfront Park, the Legacy Trail, and Siesta Key Beach, this residence offers the ultimate Sarasota lifestyle. Inside, SOARING CEILINGS and an open-concept floor plan create a bright, airy living space designed for both everyday comfort and entertaining. The sleek EUROPEAN-STYLE KITCHEN showcases quartz countertops, glossy cabinetry, NATURAL GAS cooking, a large center island, pantry, and smart pull-out storage solutions. The spacious primary suite includes custom closet built-ins and an en suite bathroom featuring dual sinks and a walk-in shower. Enjoy seamless indoor-outdoor living with a SCREENED LANAI overlooking the PRIVATE POOL, mature landscaping, and privacy wall. A natural gas connection for grilling makes outdoor entertaining effortless year-round. Built for efficiency and peace of mind with CONCRETE BLOCK CONSTRUCTION, IMPACT WINDOWS AND SLIDERS, SMART HOME FEATURES, NATURAL GAS SERVICE, WHOLE-HOUSE GENERATOR, and an attached two-car garage. An incredible opportunity to own a newer custom-built home in sought-after Arlington Park, offering lock-and-leave convenience, contemporary style, and close proximity to Sarasota's best dining, shopping, healthcare, cultural attractions, and world-renowned beaches.
Listing is courtesy of: ENGEL + VOELKERS SARASOTA (941-388-9800)
Listing Agent: Meagan Jones (941-402-7012)
4660 OCEAN BLVD #Q1, SARASOTA, FL 34242
$525,000302 Days on yellowkey MLS ID: A4659204
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1200 Built: 1971 Tax: $7,101 (2024)Community: Sea VillageCondo
Taxes:$7,101
Remarks: PRICED TO SELL! NEW impact-rated sliding glass doors were installed in June 2026, providing enhanced storm protection and complementing the home’s existing hurricane-impact windows. Experience million-dollar, direct Gulf views from this ground floor condominium in the sought-after community of Sea Village on Siesta Key. Enjoy sunsets every evening from your private lanai, just steps from the shoreline and minutes from one of the world’s top beaches. This 2-bedroom, 2-bath residence has been thoughtfully updated with a fully remodeled kitchen, tile flooring throughout, and plantation shutters. Hurricane-impact windows provide additional protection and lasting value. Additional features and upgrades include a 2021 water heater, 2022 HVAC, 2023 electrical panel, in-unit washer and dryer, designated parking, storage shed, and bike storage. Sea Village offers residents a true coastal lifestyle with a heated waterfront pool, tropical grounds, and easy access to dining, shopping, and Siesta Key’s vibrant village. Covered parking and generous guest parking make entertaining convenient. Perfect as a primary residence or seasonal retreat, this home blends unmatched views with modern upgrades in one of Sarasota’s most desirable island communities.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Halie Monde (941-735-4707)
2430 FLOYD ST, SARASOTA, FL 34239
$1,700,000Listed 06/19/2026 9:51AM MLS ID: A4697497
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2743 Built: 2025 Tax: $18,461 (2025)Community: Rustic LodgeSingle Family
Taxes:$18,461
Remarks: Set in the sought-after Arlington Park area, this exceptional 2024-built modern residence offers a rare blend of refined design, flexible living, and resort-style outdoor space. With 6 bedrooms and 4.5 baths in total, including a detached 1 bedroom, 1 bath guest house above the garage, the home is thoughtfully designed for both everyday comfort and elevated entertaining. The main residence welcomes you with bright, expansive living spaces, abundant natural light, remote-control window treatments throughout, a sleek fireplace, and effortless indoor-outdoor flow. At the heart of the home, the chef’s kitchen makes an elegant statement with crisp white cabinetry, solid-surface countertops, stainless steel appliances, a striking range hood, built-in oven, walk-in pantry, and an oversized island designed for gathering. The bedroom layout offers exceptional versatility for family, guests, work-from-home needs, or media space, while generous closet and storage space throughout the home add everyday ease. The primary suite is a private retreat, complete with dual walk-in closets and a refined sense of comfort. The detached guest house elevates the property’s flexibility even further. Positioned above the garage, it features its own bedroom, full bath, and living area, along with space that could be built out into a kitchen or kitchenette area. It is ideal for extended family, visiting guests, an au pair suite, private office, studio, or additional retreat space. Outdoors, the home is designed to live like a private Sarasota escape, with a sparkling pool, expansive paver patio, covered dining area, outdoor kitchen, balcony, and lush tropical landscaping. A detached 2-car garage, fenced yard, and two laundry rooms, one upstairs and one downstairs, provide added convenience. Located minutes from downtown Sarasota, Southside Village, Sarasota Memorial, dining, shopping, and the area’s world-class beaches, this residence delivers modern luxury, rare guest-house functionality, and an elevated lifestyle in one of Sarasota’s most desirable central locations.
Listing is courtesy of: KW SUNCOAST (941-792-2000)
Listing Agent: Banning Tibbetts (941-713-5663)
5649 WESTWIND LN, SARASOTA, FL 34231
$294,00038 Days on yellowkey MLS ID: A4693241
REDUCED by $5,000 (1.7%) on 06/06/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1169 Built: 1980Monthly Fee: $560 Tax: $2,641 (2025)Community: Villa GardensVilla
Taxes:$2,641
Elementary School: Gulf Gate Elementary
Remarks: Welcome to your hidden gem in the heart of Sarasota! This charming Westwind Lane home invites you in with a bright, open layout and tasteful updates that make it feel warm and move-in ready from day one. Step outside to your own private space—perfect for unwinding after a long day or hosting friends and family while enjoying the Florida lifestyle. Just minutes from Siesta Key and close to great shopping, dining, and daily conveniences, the location truly speaks for itself. It’s the kind of place you dream about when you think of living in Sarasota. Come see it for yourself—schedule your private showing today before it’s gone!
Listing Agent: Marina Paige (941-263-9545)
3612 S LOCKWOOD RIDGE RD, SARASOTA, FL 34239
$689,0007 Days on yellowkey MLS ID: A4696876
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2895 Built: 1962Monthly Fee: $17 Tax: $3,014 (2025)Community: South GateSpa: NoSingle Family
Taxes:$3,014
Remarks: Beautiful 4BR/3Bath Pool Home in the highly desirable Southgate neighborhood close to everything great that Sarasota has to offer. Sitting on a perfect rectangular 10,500 Sq’ lot the home boast 2895 Sq’ of indoor livingspace, offering plenty of room for multi-generational living or converting the primary suite (with 2 doors to the exterior) into a Mother-In-Law apartment or ADU (AuxiliaryDwelling Unit) as a possible income generator. The stand-up attic offers excelent additional storage or oportunity to dormer and make into additional living space. When you enter the home, you are greeted by a massive living room and tastefully updated ceramic tile on the diagonal that carries throughout the home. The open plan main living areas are complemented with spacious split bedrooms for privacy. The light and bright kitchen has 2 windows and recessed LED lighting and ample stone counters that a cook or baker will appreciate, plus upscale Samsung black stainless steel appliances, and a breakfast bar to the bonus room that has 2 large pantry closets and a built in desk with shelves. French doors lead out to the paver brick; lanai, patio and sunny pool area, on a spacious fully fenced backyard. The home is on county water and sewer and has 9.5 year old roof, 2 zones of HVAC; one is 2021 14 SEER Trane 2 ton for the primary BR side of the home, and the other is a 13 year old 15 SEER 3.5 ton Comfortmaker that is serviced regularly for the rest of the home. Large overhanging roof provides shade for passive cooling and coverage for outdoor storage. Book your private showing and scoopup this great opportunity NOW!
Listing is courtesy of: ALBERT WOOSTER & COMPANY (941-350-1220)
Listing Agent: Albert Wooster (941-350-1220)
300 GARDEN LN, SARASOTA, FL 34242
$2,790,000287 Days on yellowkey MLS ID: A4662830
REDUCED by $209,000 (7.0%) on 05/21/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3256 Built: 1975Monthly Fee: $10 Tax: $12,545 (2024)Community: Siesta Rev OfSpa: NoSingle Family
Taxes:$12,545
Remarks: A Rare Opportunity on North Siesta Key with exceptional weekly income, prime location 350 Feet of Waterfront! Discover this unique multi-family income producing single-story property on Bay Island, offering both beauty and potential. High and dry, the home remained unaffected by recent storms, with 4–5 feet of elevation to spare. Set on a tranquil, tropical lot, this historic location on Garden Lane—once home to the Siesta Key Fish Market—with easy fast access to the bay and Big Pass it is truly a boater’s and fisherman’s paradise. Just a few steps to Shell Beach and its breathtaking sunsets, minutes from the world famous Siesta Beach, Siesta Village with restaurants, shopping, nightlife, quick access to downtown, and St. Armands Circle. You have it all! The property features a classic Florida ranch-style 4-bedroom, 2-bathroom home with a pool, large deck, and lush backyard designed for entertaining, plus a detached 2-bedroom, 2-bathroom guest house. Whether you choose to renovate, rebuild, or divide the lot (buyers to verify with the City), the possibilities are endless with this property!
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Holly Parry (941-809-8050)
6448 HOLLYWOOD BLVD, SARASOTA, FL 34231
$3,995,000Listed 06/19/2026 8:43AM MLS ID: A4697076
0 Days Off yellowkey (back on 6/19/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4055 Built: 1991 Tax: $15,348 (2025)Community: Pine Shores Estate 7Th SecSpa: YesSingle Family
Taxes:$15,348
Remarks: Under contract-accepting backup offers. Exceptional waterfront living awaits in this extensively updated three-story Intracoastal estate offering 113 feet of deep-water frontage, no fixed bridges to the Gulf, and less than one mile to world-renowned Siesta Key Beach. Designed for both luxury and lifestyle, this 4-bedroom, 4.5-bath residence encompasses 4,055 air-conditioned square feet and 6,129 total square feet of thoughtfully curated living space. A boater's dream, the property features a new 20,000-pound boat lift, 113 feet of new Trex dock, and a 7,000-pound double jet ski lift with direct access to Sarasota Bay and the Gulf of Mexico. The resort-style outdoor environment has been transformed with more than $250,000 in professional landscaping by Plant Source, featuring lush tropical gardens, bamboo privacy hedges, coconut and royal palms, premium turf, a propane fire pit, tiki torches, a sparkling pool, and multiple spaces for waterfront entertaining. A custom dual-entry metal privacy gate provides a grand and private arrival. Inside, the residence showcases engineered hardwood flooring throughout, impact-rated windows and doors, remote-controlled blinds, a whole-home water purification system, and a private elevator servicing all three levels. The recently redesigned kitchen and interior spaces were professionally reimagined by Mindy Webb Design & Blu Interiors, blending timeless coastal elegance with modern luxury. The first floor offers a three-car garage, gym, recreation room or office, and hurricane-rated sliding glass doors opening to the pool and waterfront living areas. The second floor serves as the heart of the home with expansive gathering spaces and an outdoor lounge area ideal for enjoying Sarasota's year-round sunshine. Occupying the top level, the private primary suite features a waterfront balcony with breathtaking Intracoastal and sunset views, creating the ultimate owner's retreat. Adding flexibility and value is a detached pool house complete with a new metal roof, impact windows and doors, and its own mini-split system. Comfort is ensured throughout the property with three separate air-conditioning systems serving the main residence, plus additional mini-splits in the gym and auxiliary spaces. Ideally located just over the South Siesta Key Bridge, this exceptional waterfront estate offers a rare combination of deep-water boating, designer renovations, resort-style outdoor living, and convenient access to Siesta Key Beach, dining, shopping, and all that Sarasota has to offer.
Listing is courtesy of: NCC PROPERTIES LLC (941-924-1868)
Listing Agent: Morgan Marziali (941-806-7214)
3229 BENEVA RD #203, SARASOTA, FL 34232
$190,00026 Days on yellowkey MLS ID: A4694705
REDUCED by $5,000 (2.6%) on 06/19/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 964 Built: 1978 Tax: $2,064 (2025)Community: Village Brooke Sec 3Condo
Taxes:$2,064
Remarks: Experience the perfect blend of modern style, privacy, and Sarasota convenience in this beautifully renovated second-floor condo at Village Brooke Condominium. Ideally positioned with no upstairs neighbors, this move-in-ready residence offers exceptional privacy and peaceful living just 6 miles from the world-famous Siesta Key Beach. Completely renovated from top to bottom, this beautiful condo features new flooring, fully updated bathrooms, modern recessed lighting, and a designer kitchen showcasing brand-new cabinetry, quartz countertops, and new stainless steel appliances. Every detail has been thoughtfully upgraded to create a fresh, contemporary feel rarely found in Village Brooke. Enjoy true maintenance-free living with the condo association covering exterior maintenance, grounds maintenance, private roads, cable TV, water, and sewer. Residents also enjoy resort-style amenities including two community pools, tennis courts, and shuffleboard courts — all within a beautifully maintained, centrally located Sarasota community close to shopping, dining, downtown Sarasota, and Florida’s Gulf Coast beaches. Whether you’re searching for a full-time residence or winter retreat, this fully updated condo delivers style, convenience, and value in one of Sarasota’s most desirable locations.
Listing Agent: Kathy Vandorne (941-275-3934)
5780 MIDNIGHT PASS RD #407, SARASOTA, FL 34242
$1,100,000Listed 06/18/2026 10:08PM MLS ID: A4697559
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1361 Built: 1979 Tax: $9,178 (2025)Community: Gulf & Bay ClubSpa: YesCondo
Taxes:$9,178
Remarks: Welcome home to a fully updated, fully furnished 2 bedroom 2 bathroom beach oasis! Located in the heart of Siesta Key at the exclusive upscale Gulf & Bay Club. Featuring costal decor with modern neutral colors.This unit is nestled in B Building with direct beach access which is just steps away from your front door. Enjoy breath taking sunsets from your personal balcony or head down to the private beach for an up close view of the #1 beach in the US. The sandy white powder stretches 800 feet across this pristine 32 acre meticulously cared for tropical community. You will be impressed with world class amenities offered at Gulf & Bay Club. Enjoy the comfort of 24 hour gated security, heated pools, a fitness center, dry saunas, hot tub, tennis courts, just to name a few. Multiple barbecues and tiki hut picnic areas are great for entertaining your guests. The amenities don’t stop there, the club house has a library, bar, pool table and TV's all for your enjoyment. Not to mention the electric car charging stations and car wash on grounds. You are moments away from Siesta Village to enjoy alfresco dining with live music, specialty shopping and more! Take a short trip to the mainland and discover theater, art and fine dining. This is the island resort lifestyle you have been looking for, don't let your chance of fine beach living slip away.
Listing Agent: Sylvia Wilk (630-863-1825)
1387 HARBOR DR, SARASOTA, FL 34239
$5,590,000Listed 06/19/2026 7:22AM MLS ID: A4697052
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4013 Built: 1950Monthly Fee: $13 Tax: $20,477 (2025)Community: Harbor AcresSpa: YesSingle Family
Taxes:$20,477
Remarks: Pre-Construction. To be built. Welcome to effortless coastal luxury in the coveted Harbor Acres neighborhood, where timeless glamour meets breezy, tropical elegance. The Royal Palm is Heritage Builder’s latest creation. The Palm Beach–style residence is a masterclass in relaxed yet refined living—light-filled, airy, and designed for seamless indoor-outdoor enjoyment. Framed by lush, palm-lined landscaping and defined by its crisp, clean aesthetic, this 4-bedroom, 4 full bath, and 1 half bath home offers a serene, resort-like lifestyle. Inside, soft neutrals, pops of color, natural textures, and polished finishes create an inviting, ocean-kissed atmosphere that feels both elevated and effortlessly comfortable. The primary suite, thoughtfully located on the main level, is a true private retreat—spacious and serene, featuring two walk-in closets and a spa-inspired ensuite bath with a freestanding soaking tub and large glass-enclosed shower. A second guest suite downstairs provides flexibility and comfort for visitors, while an elevator ensures convenient access to every level. Upstairs, a VIP experience awaits. The luxurious suite with a private balcony offers tranquil treetop views, complemented by an ensuite with dual vanities. Designed for both relaxation and entertaining, the upper level also features a media room with a wet bar and a second utility space, enhancing both function and ease of living. Step outside into your own private, resort-style oasis, where a sparkling open-air pool is surrounded by lush, mature landscaping that creates a sense of serenity and seclusion. Framed by swaying palms and vibrant greenery, the outdoor living spaces feel both inviting and tranquil—perfect for sun-soaked afternoons, al fresco dining, or relaxed evenings under the stars. Every detail is designed to capture that breezy, tropical elegance, making it easy to feel at home in a setting that lives like a luxury retreat. Ideally located in the heart of Harbor Acres, this residence offers unparalleled access to Sarasota’s most desirable destinations. Just minutes from downtown, Selby Gardens, and the Gulf’s world-renowned beaches, you’ll enjoy the best of coastal living. Nearby Southside Village adds to the charm with its fun, friendly atmosphere, boutique shopping, and local dining—bringing together convenience, community, and lifestyle in one exceptional location. Every detail of this home reflects casual sophistication and coastal chic design, blending crisp lines with organic warmth. Whether hosting guests or enjoying quiet moments, this residence embodies the essence of Palm Beach-inspired living—bright, breezy, and beautifully refined. Experience Harbor Acres at its finest—where elegance meets ease in a home designed to live like a year-round retreat.
Listing is courtesy of: HB REALTY GROUP INC. (941-378-3983)
Listing Agent: Sara Boudarga (941-321-6352)
2531 WISTERIA ST, SARASOTA, FL 34239
$2,397,00022 Days on yellowkey MLS ID: A4694903
REDUCED by $100,000 (4.0%) on 06/19/2026
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3203 Built: 2026Monthly Fee: $17 Tax: $4,502 (2025)Community: South GateSpa: YesSingle Family
Taxes:$4,502
Remarks: Perfectly positioned in the heart of the highly sought-after South Gate neighborhood, this exceptional new construction residence by Park Residences LLC masterfully blends timeless architecture, designer-curated finishes, and state-of-the-art functionality to create an extraordinary family retreat. Offering 5 bedrooms, 5 bathrooms, and an uncompromising level of craftsmanship throughout, every detail of this luxury home has been thoughtfully designed for elevated everyday living. From the moment you enter, you are welcomed by refined interiors highlighted by 7 1/4-inch white oak engineered hardwood flooring flowing throughout, complemented by level 4 drywall finishes, custom feature walls, and stunning Visual Comfort lighting and ceiling fans, hand-selected by our interior designer. A dramatic living area showcases a sleek horizontal fireplace flanked by custom shelving creating a warm yet elegant focal point ideal for entertaining or relaxing with family. The gourmet chef’s kitchen is both elegant and functional, featuring custom white oak soft-close cabinetry, exquisite quartzite surfaces, a custom-built pantry, and a premium suite of luxury appliances. Culinary enthusiasts will appreciate the Thermador 48-inch built-in smart French door refrigerator/freezer with integrated custom paneling, Thermador dishwasher with custom cabinetry front, Fisher & Paykel 48-inch induction range with convection oven, and Sharp smart microwave drawer. Every element has been selected to combine beauty, innovation, and performance seamlessly. A custom staircase with 1 1/4-inch solid wood stair treads, beautifully stained and brushed, adds architectural character while leading to spacious secondary living areas and bedrooms. Custom closets throughout the home provide exceptional organization and storage, while pre-wiring for sound allows for effortless integration of modern smart-home living. Built with superior quality and efficiency in mind, the residence features PGT impact windows and Thermatru doors, spray foam insulation in the roof deck, garage, and lanai ceilings, and a durable steel tile roof with a lifetime warranty. Two Daikin 15 Seer heat pump air conditioning systems with Nest thermostats provide year-round comfort, while two water heating systems — including a tankless instant hot water heater and a 55-gallon Rheem Gladiator with leak detection — ensure convenience and peace of mind. Outdoor living is equally impressive with a resort-inspired heated saltwater pool and spa featuring a gunite finish, elegant waterline tile, sun shelf, autofill system, and expansive marble pool decking. A 6ft fully fenced creates a private oasis perfect for entertaining, pets, or family gatherings. Combining luxury finishes, advanced construction quality, and impeccable design in one of the area’s most desirable family neighborhoods, this remarkable South Gate residence offers a rare opportunity to own a truly remarkable new construction home where sophistication, comfort, and functionality come together effortlessly.
Listing is courtesy of: SARASOTA TRUST REALTY COMPANY (941-366-1619)
Listing Agent: Renee Preininger (941-400-4235)
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