Location: Sarasota
Keyword(s): Sarasota High
Keyword(s) High School: Sarasota High
Do Not Show Listings
459 WINGFIELD DR, SARASOTA, FL 34237
$1,249,00039 Days on yellowkey MLS ID: A4685397
0 Days Off yellowkey (back on 4/2/2026)
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2108 Built: 2021Monthly Fee: $297 Tax: $10,780 (2025)Community: Payne Park VillageSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,780
Elementary School: Alta Vista Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Under contract-accepting backup offers. This is the one * WELCOME TO YOUR BEAUTIFULLY DESIGNED SINGLE FAMILY HOME IN RARELY AVAILABLE PAYNE PARK VILLAGE, IN THE HEART OF DOWNTOWN SARASOTA * If you want PRIVACY this home is for you! * SPACIOUS BACKYARD with a Covered Lanai * Custom Landscaping with Coconut Palm and 3 sitting areas to relax in your slice of paradise * Outdoor Shower * Plenty of room to add an outdoor grill * Your backyard gate is just steps away to The Legacy Trail * This is a ONE OF A KIND SETTING and definitely a PREMIUM UPGRADED LOCATION * No neighbors on 3 sides * Dead end street with no through traffic * Built in 2021 with HURRICANE IMPACT GLASS WINDOWS & DOOR, this home has been THOUGHTFULLY REIMAGINED BY THE CURRENT OWNER with NEW Quartz Countertops, NEW Paint, NEW Custom Designs Throughout, NEW Restoration Hardware Lighting – the list goes on & on * Chef’s Kitchen showcases UPGRADED Thermador Stainless Steel Appliances, Built-in Oven, Separate Cook-top, and Wine Cooler * The Kitchen is open to the Great Room & Dining Room * You will enjoy an ABUNDANCE OF NATURAL LIGHT with additional windows since this is an END UNIT HOME * 3 Bedrooms & 3.5 Baths * Wood Floors * 3 Levels * A true Primary Retreat with Pecky Cypress Ceiling & a Spa-style Bath featuring a Free-standing Tub, Walk-in Shower, Dual Vanities & SPACIOUS Walk-in Closets * A very nice Laundry Room with additional counter-space * Private Setting * 2 Car Garage on a dead end street * You will NOT find another home like this at this price * LOW HOA FEE * NO CDD FEE * Living in Payne Park Village places you in one of Sarasota’s most vibrant & centrally located neighborhoods, where urban convenience meets expansive green space and is nearby the popular Legacy Trail. Residents enjoy exclusive access to a private community amenity center with a Heated Pool and Spa, while Payne Park itself offers tennis courts, pickleball, disc golf, skate park & a playground. With downtown Sarasota’s dining, arts, and cultural destinations moments from your door, this home offers a rare balance of city living, outdoor freedom, and low-maintenance luxury. * One look & you’ll fall in love *
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Ryan Brown (941-330-7774)
915 BEACH RD #318, SARASOTA, FL 34242
$599,00073 Days on yellowkey MLS ID: A4682116
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 753 Built: 1972 Tax: $4,536 (2025)Community: La SiestaCondo
Taxes:$4,536
Elementary School: Phillippi Shores Elementary
Remarks: Experience the ultimate Siesta Key lifestyle in this turnkey furnished, beautifully decorated 2-bedroom, 1-bathroom condo in the highly sought-after La Siesta Condominiums! Located on the third floor of Building C, this unit boasts stunning views of the community pool and the world-famous Siesta Key Beach—just steps away across the street! With 753 sq. ft. of thoughtfully designed space, this condo is fully equipped for personal enjoyment or an income-producing rental. The primary bedroom features a king-size suite, while the guest room is set up with two twin beds, both sharing a hall bath with a tub/shower combination. The open-concept living space extends to a screened patio, where you can relax and enjoy the tropical breeze. This unit is move-in or rental-ready, featuring hurricane impact windows and doors, a new roof, updated A/C, thermostat, and electrical. Additional conveniences include an elevator, a covered parking space, guest parking, and a private ground-floor storage closet, perfect for keeping your beach gear ready to go! Each building also has a shared washer and dryer for residents. La Siesta offers resort-style amenities, including a heated pool, BBQ areas, shuffleboard, a clubhouse, a fitness room, and on-site management for easy guest check-ins and check-outs. The condo is part of La Siesta’s rental program and is also listed on Airbnb, allowing for weekly rentals with a strict 25+ minimum rental age. Owners can live here full-time, use it as a vacation retreat, or take advantage of its strong rental potential. Ideally located just minutes from Siesta Key Village, you’ll have easy access to local shops, restaurants, and entertainment, all while enjoying one of the most beautiful beaches in the country. Whether you’re looking for a beachside getaway or a high-performing investment property, this is a rare opportunity to own in one of Siesta Key’s most desirable communities. Schedule your private showing today!
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Joseph Millslagle (941-815-3461)
3625 JACINTO CT, SARASOTA, FL 34239
$600,00043 Days on yellowkey MLS ID: A4686033
REDUCED by $25,000 (4.0%) on 04/02/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1008 Built: 1957 Tax: $707 (2025)Community: GranadaSingle Family
Taxes:$707
Elementary School: Southside Elementary
Remarks: This property offers an opportunity to secure a homesite in the highly desirable West of Trail neighborhood. Situated on a quiet residential street, this property presents the chance to build a custom residence in a location known for its charm, convenience, and long-term value. The existing structure on the property is a modest single-family home, but the true value here lies in the land and the prime setting it provides. Buyers looking to design and build their dream home will appreciate the opportunity to start fresh in a neighborhood where new construction and luxury homes continue to transform the streetscape. West of Trail is widely regarded as one of Sarasota’s most sought-after mainland locations. Nestled between Sarasota Bay and Tamiami Trail, the area is known for its picturesque, tree-lined streets, historic charm, and proximity to many of the city’s most desirable destinations. One of the biggest draws of this location is its outstanding convenience. The property is just minutes from Southside Village, a vibrant and walkable district known for its boutique shops, restaurants, and local cafés. Downtown Sarasota is also only a short drive away, offering theaters, art galleries, marina views, and an active cultural scene. For beach lovers, this homesite is ideally positioned close to Siesta Key, world-famous for its powdery white quartz sand and stunning Gulf sunsets. Families are also drawn to the area because of the highly regarded local school district, including Southside Elementary.
Listing is courtesy of: CORCORAN DWELLINGS REALTY (941-200-4663)
Listing Agent: Marc Rasmussen (941-200-4663)
1349 GRAND BLVD #1006, SARASOTA, FL 34232
$325,000170 Days on yellowkey MLS ID: A4670997
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1308 Built: 1972 Tax: $849 (2024)Community: Forest Pines 10Villa
Taxes:$849
Tax Year: 2024
Remarks: Welcome to Forest Pines, a friendly 55+ community in the heart of Sarasota’s Pinecraft area. This light-filled villa offers a comfortable, open layout with tile flooring throughout and spacious bedrooms for easy living. The floor plan includes a dedicated laundry room with utility sink, covered entry and carport with extra storage, and a paver patio out back for relaxing outdoors. The primary suite features a makeup vanity and generous closet space. Added peace of mind: this property is not in a flood zone and has had no flooding during recent storms. Residents enjoy a low-maintenance lifestyle with access to community amenities and a welcoming neighborhood atmosphere. Association fees include cable TV, common area taxes, community pool, escrow reserves, lawn and grounds care, management, pool maintenance, and private road upkeep. Conveniently located just minutes from restaurants, shopping, parks, downtown Sarasota, beaches, and The Legacy Trail, this villa offers comfort, value, and an easy Florida lifestyle in one of Sarasota’s most walkable and social locations.
Listing is courtesy of: HARRY ROBBINS ASSOC INC (941-924-8346)
Listing Agent: Marlin Yoder (941-893-7406)
3317 PINE VALLEY DR, SARASOTA, FL 34239
$599,900236 Days on yellowkey MLS ID: A4663718
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
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)
3247 ALEX FINDLAY PL, SARASOTA, FL 34240
$995,000193 Days on yellowkey MLS ID: A4668327
1 Days Off yellowkey (back on 4/2/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2228 Built: 1991Monthly Fee: $369 Tax: $9,385 (2024)Community: Laurel Oak Estates Sec 02Single Family
Taxes:$9,385
Elementary School: Tatum Ridge Elementary
Middle School: McIntosh Middle
Remarks: Under contract-accepting backup offers. Prestigious Laurel Oak Estates, this beautiful private Lakefront home enjoys serene water views and the added backdrop of an adjacent natural preserve, creating a peaceful, secluded setting on an expansive 0.49 homesite with room for future additional expansion. Situated behind the guard-gated community of Laurel Oak Estates on a cul-de-sac, this three-bedroom, two-bath residence plus den features a bright, open great room floor plan with neutral colors and a new gourmet kitchen with granite countertops, white cabinetry, and a large island perfect for entertaining. Your primary retreat overlooks the screened, covered lanai with desirable eastern exposure and a spacious pool and sparkling lake—ideal for enjoying Florida’s indoor-outdoor lifestyle. Updates include a newer insulated tile roof, pool re-surfaced, heat pumps for house and pool, porcelain flooring, light fixtures, entry doors, irrigation controls, abundant natural light, and a two-car side-entry garage with an expansive driveway. Convenient to shopping, dining, churches, and top-rated schools, including The Classical Academy for grades pre-school through twelve grade. Optional Laurel Oak Country Club membership offers two Championship golf courses, Har-Tru tennis, Pickleball, dining, an active social calendar, and reciprocal privileges with Bird Key Yacht Club. Ownership includes priority placement on the Laurel Oak Country Club membership waitlist. Move-in ready and ready to enjoy the best of Florida living. Come live the Lifestyle at Laurel Oak Estates!
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-907-9541)
Listing Agent: Linda Dooley (941-400-7359)
1825 PARAKEET WAY #503, SARASOTA, FL 34232
$182,50081 Days on yellowkey MLS ID: A4680435
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1049 Built: 1970 Tax: $2,324 (2025)Community: Vistas On BenevaCondo
Taxes:$2,324
Remarks: Worry free, hassle free, and arguably the best view in the community with a golf course views from the back and pool views from the front. This two-bedroom, two-bath, second floor condo in Vistas on Beneva has had all the important mechanical updates and upgrades as well as move-in ready cosmetics including fresh paint, and freshly cleaned carpet and tile, newer kitchen appliances, lights, fans, deck and screen, newer toilets and modern bathrooms. You’ll have peace of mind with impact windows throughout, a new, upgraded electrical panel with surge protection, newer AC with transferable warranty, and a new roof on the building. The lifestyle is unbeatable at this price. You’ll enjoy tranquil golf course views from the deck, views of the well-kept community pool, easy access to the fitness room and pool, storage for your bicycles and easy access to The Legacy Trail. This condo comes with a carport parking spot (rare in this community). Condo fee of $652 per month includes the use and maintenance of the recreational facilities (pool, fitness room), sewer and water, bicycle storage, pest control and insurance for the building, grounds maintenance, and an on-site manager. Two pets are allowed. Owners may rent their units out for a minimum of 1 month, up to 3 times per year. Vistas on Beneva is conveniently located between Bahia Vista and Webber, offering quick access to Siesta Key, downtown Sarasota, Lido Key, St. Armands Circle, Sarasota Memorial Hospital and several golf courses.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Christine Pope (941-685-5565)
24 SANDY COVE RD #A6-D, SARASOTA, FL 34242
$469,00078 Days on yellowkey MLS ID: A4680784
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 561 Built: 1968 Tax: $4,201 (2025)Community: Sandy CoveCondo
Taxes:$4,201
Remarks: This freshly updated turnkey furnished 1 bed + loft pet-friendly condo is ready for its new owner! The unit sits high and dry on the second floor and has a small loft with a queen-sized bed, a wood-burning fireplace, a main bedroom with a separate mini split AC unit, and ensuite bathroom with shower. Plenty of natural light and a large, newly refinished balcony overlooking the spring-fed lake. Updates include refinished kitchen cabinetry, quartz countertops, cooktop, moveable island with genuine butcher-block top, built-in trash and recycling cabinet, and a breakfast bar with seating for 4, and hard-wearing luxury vinyl plank floors throughout the main living/bedroom area. This unit also benefits from a brand-new standing seam metal roof. Sandy Cove is a highly sought-after old Florida-style community located just north of Siesta Key Village. Relax and enjoy the pristine white quartz sand 350 ft. stretch of private Gulf-front beach in a natural Old Florida setting. Enjoy the morning sun from your balcony. Come experience the true experience of old Florida with the Sandy Cove community, designed by the renowned Sarasota School of Architecture master Frank Folsom Smith. You will have a covered parking space with a storage closet for beach chairs and bikes, and there is kayak storage on site. Impact windows and sliders. Stack washer and dryer in unit. Just bring your beach towel and move right in!
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-907-2000)
Listing Agent: Bev Murray (941-724-4995)
1864 GOLDENROD ST, SARASOTA, FL 34239
$1,695,000102 Days on yellowkey MLS ID: A4676645
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2307 Built: 2003 Tax: $7,463 (2024)Community: Poinsettia Park 2Single Family
Taxes:$7,463
Remarks: BEST VALUE WEST OF THE TRAIL! OVER $250,000 PRICE IMPROVEMENT! This dazzling custom-built, single-level pool home is situated in the desirable "flower streets”, west of the trail in Sarasota. Featuring a new, 3 color clay tile roof and Mediterranean style design this home has timeless style combined with modern luxury. Upon entering the double doors of this one-story retreat, you will notice the open layout and quality appointments that abound with tray and coffered ceilings, custom built-ins and niches, gas fireplace, gorgeous and rare coquina stone floors. This 4 bedroom (one a custom designed office), 3 bath, 3-car garage home features a new island kitchen with custom and glass front cabinets, stainless steel appliances, decorative backsplash and beautiful quartz counters. The tranquil primary retreat overlooks the lanai and pool and features a walk-in closet with built in closet system, wood floors and an incredible ensuite bath. This newly renovated primary bath exudes luxury with custom cabinetry, upscale finishes, and features a walk-in shower for a spa-like experience. The split floor plan showcases two additional guest bedrooms (one with a custom Murphy bed and office) each with access to newly renovated bathrooms. The high ceilings and 3 sets of sliding glass doors flood the open floor plan with natural light, while custom finishes and soft contemporary décor create an atmosphere of effortless sophistication. The very private lanai with a screened pool, new pool heater, fiber optic lighting, Pebble tec finish, pool bath and outdoor shower is surrounded with lush vegetation, perfect for entertaining and outdoor relaxation. The paver driveway and side-entry 3 CAR garage adds additional built-in storage, a 2nd refrigerator and fabulous curb appeal. Within city limits, this residence offers the option of a part-time stay, allowing for potential short term rental income. When you want to enjoy the neighborhood, you are minutes away from downtown Sarasota’s cultural scene, Siesta Key Beach, Southside Village shops and restaurants. World-class health care is located steps away at Sarasota Memorial Hospital’s main campus. This home has it all -- a sanctuary feel AND all the amenities you desire at your fingertips.
Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE (941-556-9100)
Listing Agent: Jan Jordan (941-737-4169)
5300 OCEAN BLVD #202, SARASOTA, FL 34242
$1,130,00099 Days on yellowkey MLS ID: A4678274
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1372 Built: 1973 Tax: $9,941 (2025)Community: Terrace EastCondo
Taxes:$9,941
Remarks: Step inside and unwind in this updated, turnkey luxury condominium offering nightly sunset views of the #1 beach in the country. This is a rare opportunity to own a condominium in the vibrant heart of Siesta Key, walk to all the amenities and charm that Siesta Key village offers. The property is just steps from the world-famous quartz sands of Siesta Key Beach. Tastefully decorated and truly move in ready, this coastal retreat features a beautifully updated kitchen with custom cabinetry, granite countertops, tile backsplash, stainless steel appliances, crown molding, and thoughtful designer finishes. Luxury vinyl flooring flows throughout the condominium, creating a cohesive and low maintenance living space ideal for beachside living. Both bathrooms have been updated and showcase tile showers with elegant quartz sinks. Two spacious balconies provide the perfect setting to enjoy stunning Gulf sunsets, entertain family and friends, or take in the vibrant island atmosphere below. The island lifestyle is at your doorstep with easy access to local restaurants, live music, boutique shopping, and even a grocery store within .2 of a mile. Located in the iconic Terrace East, this 24-hour secure building offers a welcoming common area for residents and guests. The community has recently enhanced its curb appeal with updated landscaping and beautifully refreshed grounds, creating a true resort style ambiance. Residents enjoy a spacious sparkling pool with new pool furniture, an exercise room, a private tennis/pickleball court, and new stainless steel outdoor grills perfect for entertaining. Whether you are searching for a primary residence, second home, or vacation getaway, this condominium delivers luxury, comfort, and exceptional walkability in one of Florida’s most desirable beach destinations. Experience the best of Siesta Key beach lifestyle in an elevated retreat that combines iconic location, modern updates, and outstanding amenities.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Diane Goodwin (941-706-6620)
5770 MIDNIGHT PASS RD #404, SARASOTA, FL 34242
$1,350,00060 Days on yellowkey MLS ID: A4683014
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1337 Built: 1980Monthly Fee: $1,647 Tax: $10,853 (2025)Community: Gulf & Bay Club Ph 3Condo
Taxes:$10,853
Remarks: Under contract-accepting backup offers. Welcome home to Gulf & Bay Club, the premier condominium community on Siesta Key Beach. Enjoy stunning views of the freshwater lake, fountains, island lagoon, swimming pools, sandy beach, and the Gulf of America from your private lanai. Step into this beautifully remodeled Turnkey Furnished, 2-bedroom, 2-bath beach condo offering modern finishes and thoughtful upgrades throughout. The kitchen is a true standout with quartz countertops and tile backsplash, solid wood soft-close cabinets with pull-out drawers, GE stainless steel appliances, a built-in desk, and a spacious island with ample storage. Enjoy the durable tile flooring throughout, plantation shutters, solid core doors, and recessed lighting that enhances the home’s clean, contemporary style. A new impact-rated entry door adds peace of mind. The private laundry room features full-size LG washer and dryer along with plenty of built-in storage cabinets. In addition to the amazing views, the primary suite also offers a well-appointed bathroom with dual sinks, generous built-in storage, and a walk-in shower. The guest bedroom has two full-size beds and includes built-in drawers for added convenience. Relax on the screened-in lanai and enjoy your morning coffee or evening cocktails. Gulf & Bay Club spans 32 acres with 800 feet of private beach and offers unmatched amenities, including three heated pools, indoor spa, dry saunas, tennis, pickleball, shuffleboard, billiards, a commercial-grade fitness center, BBQ and picnic areas, electric car charging stations, a car wash area, two clubhouses, a rentable guest suite, and 24-hour gated security. Wi-Fi is available throughout the property. Located adjacent to the world-famous Siesta Key Beach, ranked #1 in the U.S. by TripAdvisor for its powdery white quartz sand. This property offers a rare opportunity to enjoy resort-style living in one of Florida’s most coveted coastal communities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Tina Johns (941-323-4775)
743 STONECREST DR, SARASOTA, FL 34232
$719,999318 Days on yellowkey MLS ID: A4654945
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2197 Built: 2003Monthly Fee: $50 Tax: $3,149 (2024)Community: The Oaks At Woodland Park Ph 2Single Family
Taxes:$3,149
Elementary School: Fruitville Elementary
Remarks: Welcome to a hidden gem in the heart of Sarasota, nestled within an intimate community of just 77 homes. This beautifully maintained four-bedroom residence offers the perfect blend of comfort, style, and Florida charm. With an open-concept layout and warm maple wood flooring throughout the main living spaces, it’s ideal for both relaxed family living and entertaining guests. The kitchen is a dream for home chefs, featuring 42” cabinetry, granite countertops, under-cabinet lighting, a walk-in pantry, and a smart layout that makes meal prep a breeze. The family room, formal dining, and living areas flow effortlessly together, creating a welcoming space full of natural light. The oversized primary suite serves as a true retreat, offering direct access to the lanai through sliding glass doors. The ensuite bathroom boasts double vanities, a relaxing garden tub, and a sleek glass-enclosed walk-in shower. Each of the additional bedrooms is generously sized, with one currently being used as a home office. A guest bathroom conveniently opens to the pool area—perfect for rinsing off after a swim. Step outside to your private backyard oasis, where a pavered lanai with wood-paneled ceilings provides the ideal setting for alfresco dining or simply unwinding. A heated pool and spa elevate everyday living, making it easy to enjoy Florida’s sunny lifestyle year-round. Lush landscaping adds to the tranquil ambiance. Ideally situated near both downtown Sarasota and I-75, this location offers unmatched convenience. And with the Gulf Coast’s world-renowned beaches just a short drive away, this home truly offers the best of Sarasota living. Don't wait, schedule your showing today!
Listing is courtesy of: SARASOTA LAND AND HOMES LLC (941-320-6687)
Listing Agent: James Hirschman (941-320-6687)
3217 TEAL AVE, SARASOTA, FL 34232
$319,90059 Days on yellowkey MLS ID: A4682931
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1096 Built: 1956 Tax: $2,238 (2025)Community: Sarasota SpringsSingle Family
Taxes:$2,238
Elementary School: Brentwood Elementary
Remarks: Welcome to your move-in-ready Sarasota home offering easy, low-maintenance living with terrazzo flooring throughout and a bright Florida room that adds flexible space for dining, lounging, or work-from-home needs! A newer roof and other upgrades await! A spacious backyard provides room to relax or customize to your vision. Centrally located near shopping, dining, Downtown Sarasota, and top rated beaches, this property is an excellent option for an income-producing rental, a first-time homebuyer, or someone looking to downsize without sacrificing comfort or convenience. Call to schedule a time to see this fantastic property for yourself!
Listing Agent: Ryan Miller (941-954-6925)
1035 SEASIDE DR #404, SARASOTA, FL 34242
$2,650,000155 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 SeasideCondo
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 Agent: Jeff Lauer (941-441-6555)
111 GOLDEN GATE PT #802PH, SARASOTA, FL 34236
$5,995,00099 Days on yellowkey MLS ID: A4678103
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3576 Built: 2024 Tax: $77,424 (2024)Community: EvolutionCondo
Taxes:$77,424
Middle School: Booker Middle
Remarks: Now offered with the exceptionally curated selection of designer furnishings valued at over $350,000, this rare opportunity allows you to own the complete luxury lifestyle—furnished and move-in ready, (excludes artwork and personal effects.) Asking $5,995,000 over $1,250,000 below what the sellers have into this UNMATCHED VALUE penthouse at The Evolution is downtown Sarasota's most exclusive high-rise opportunity - and is just steps away from dining and downtown living. Builder William Voller said about Evolution, "It's a landmark in Sarasota! We are very proud of this building." This one-of-a-kind, TOP-FLOOR PENTHOUSE spans 3,527 SQ FT of interior living plus 562 SQ FT of wraparound TERRACE SPACE across THREE generous balconies for endless possibilities of indoor/ outdoor living. Offering FOUR BEDROOMS plus a DEN and 4.5 BATHS, this residence provides the comfort of a single family home with the elegance of HIGH-RISE LIVING. Sweeping NORTH, EAST, and SOUTH WATER VIEWS showcase SARASOTA BAY, the GULF, MARINA, and the CITY SKYLINE. FLOOR-TO-CEILING WINDOWS fill the home with natural light and allow year-round coastal breezes, and designer LUTRON ELECTRONIC SHADES grace each window, allowing privacy with ease. Interior features include ONYX QUARTZ COUNTERTOPS, PORCELAIN TILE SLABS, oversized PORCELAIN FLOORING, DESIGNER LIGHT FIXTURES, and CUSTOM EUROPEAN CABINETRY in the kitchen, baths, and closets. The PRIMARY SUITE features SILK WALLPAPER, and a SPA-INSPIRED BATH with dual sinks, a freestanding soaking tub, and onyx quartz and porcelain slab finishes. The CHEF'S KITCHEN includes WOLF APPLIANCES, sub-zero fridge-freezer with filtered water feature, induction cooktop, steam oven, built-in coffee station, a wine refrigerator, and a HIDDEN WALK-IN PANTRY. Imported European fixtures complete the space. Enjoy THREE WRAPAROUND TERRACES for ALFRESCO DINING, YOGA, or SUNSET COCKTAILS. The unit includes a DEEDED PRIVATE TWO-CAR GARAGE and is MOVE-IN READY with every upgrade imaginable. Community amenities at THE EVOLUTION include a POOL WITH OUTDOOR KITCHEN, FITNESS CENTER, YOGA ROOM, SAUNA, CLUB ROOM, and a ROOFTOP TERRACE with PANORAMIC VIEWS, OUTDOOR LOUNGE, SPA, and FIREPLACE. Experience the pinnacle of WATERFRONT LUXURY in DOWNTOWN SARASOTA's largest and most exclusive penthouse residence at THE EVOLUTION, a boutique community designed by architect MARK SULTANA, DSDG. With only 20 RESIDENCES, this is a rare opportunity to own one of Sarasota's most exclusive penthouses. Schedule your private tour today and experience the ultimate in penthouse living. Square footage developer plans. Buyer to verify dimensions. Golden Gate Point improvement and maintenance built into taxes.
Listing Agent: Melissa Gissinger (941-404-2722)
2227 GROVE ST, SARASOTA, FL 34239
$375,00059 Days on yellowkey MLS ID: A4683681
0 Days Off yellowkey (back on 4/1/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1002 Built: 1957 Tax: $4,790 (2025)Community: South GateSingle Family
Taxes:$4,790
Remarks: Discover timeless charm at 2227 Grove Street, Sarasota, FL 34239 a stunning mid-century modern gem infused with an authentic Old Florida vibe. Step inside to admire the beautifully preserved original terrazzo floors, radiating the character of the 1950s. Nestled in a prime location, this home offers effortless access to the pristine beaches and vibrant downtown Sarasota, perfectly blending classic style with modern convenience. Your slice of Sarasota paradise awaits.
Listing Agent: Robert Krasow (941-363-6507)
1856 WOODHAVEN CIR, SARASOTA, FL 34232
$575,00038 Days on yellowkey MLS ID: A4686039
1 Days Off yellowkey (back on 4/1/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1486 Built: 1979Monthly Fee: $18 Tax: $5,642 (2025)Community: TamaronSingle Family
Taxes:$5,642
Remarks: Welcome to your private poolside retreat in the desirable Tamaron community of Sarasota. This beautifully updated 3-bedroom, 2-bath home offers a seamless blend of comfort, style, and Florida outdoor living. From the moment you step inside, you’re greeted with tranquil pool and spa views, available from nearly every room. The fully fenced backyard is a true oasis; a setting that creates both privacy and serenity. Start your mornings in the spacious primary suite, where sliding glass doors lead directly to the pool, and enjoy the convenience of an ensuite bath and walk-in closet. Designed for both everyday living and entertaining, the open split floor plan features bamboo flooring throughout the main living areas and a warm, inviting layout. The kitchen is thoughtfully updated with stainless steel appliances, abundant cabinetry, under-cabinet lighting, and granite counters. It flows effortlessly into a charming keeping room with a built-in buffet—perfect for casual dining or a relaxed conversation setting. A combined living and dining space offers additional flexibility for hosting gatherings. On the opposite side of the home, two guest bedrooms and a full bath provide comfort and privacy for family or visitors. Additional features include a 2-car garage with laundry and extra storage, central vacuum system, hurricane shutters, and outdoor storage sheds. Major updates include a new roof and fully owned solar panels (2024), adding both value and energy efficiency. Tamaron residents enjoy a peaceful neighborhood setting with a nature preserve, ponds, walking trails, sidewalks, and a playground. Ideally located just minutes from shopping, dining, downtown Sarasota, the Legacy Trail, and world-renowned Gulf Coast beaches. This is more than a home—it’s a lifestyle. Schedule your private showing today.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Eileen Saunders (662-404-0816)
5855 MIDNIGHT PASS RD #227, SARASOTA, FL 34242
$499,00098 Days on yellowkey MLS ID: TB8463933
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1056 Built: 1976 Tax: $4,947 (2025)Community: Harbor Towers Y & RCondo
Taxes:$4,947
Remarks: Have you been searching for your own slice of tropical paradise on Siesta Key? Look no further than this pet-friendly, 2-bedroom, 2-bathroom residence in the perfectly located Harbor Towers Yacht & Racquet Club. This updated home feels fresh and inviting with new luxury vinyl wood-plank style flooring and brand-new hurricane impact-resistant windows for total peace of mind. Harbor Towers is a well-established community situated right in the heart of "The Key," just across the way from the world-famous Siesta Key Beach and a short distance from vibrant shopping and dining. Life here feels like a permanent vacation with access to a resort-style swimming pool, an oversized hot tub, three Har-Tru tennis courts, a fitness center, and a social room with a catering kitchen. Boaters will especially love the on-site marina, where boat slips are available on a first-come, first-served basis for a nominal monthly hook-up fee. Whether you are looking for a primary residence, a seasonal getaway, or a smart investment with a documented rental history, this hidden gem is ready for you. Come and see what makes this such a special place to live!
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Steven Weiss (845-242-5473)
2456 ARDEN DR, SARASOTA, FL 34232
$379,90029 Days on yellowkey MLS ID: A4687709
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1348 Built: 1989 Tax: $4,017 (2025)Community: Sarasota SpgsSingle Family
Taxes:$4,017
Remarks: Under contract-accepting backup offers. Impeccably maintained and ideally located, this charming two-bedroom, two-bath residence is tucked in a quiet section of Sarasota Springs, offering comfort and convenience. From moment you arrive, pride of ownership is evident with a freshly painted exterior and inviting curb appeal. Go inside to a light-filled living room featuring vaulted ceilings and expansive front windows that create an airy, welcoming atmosphere. The thoughtfully designed layout offers a seamless flow, with the bedrooms privately off the main living area and a well-appointed shared bath. The heart of the home opens beautifully into a spacious dining area and an updated kitchen complete with solid wood cabinetry and granite countertops, ideal for everyday living and entertaining. At rear of the home, a cozy family room lined with windows with upgraded custom blinds provides a relaxing retreat and brings in natural views of the backyard. Just off the kitchen, the laundry area offers convenient access to the second full bath, oversized garage and direct entry to the expansive open patio. Go outside to enjoy a generously sized, fully fenced backyard, ideal for pets, play or entertaining, featuring a dedicated fire pit area for gathering under the stars. Recent updates include a new roof (2021) and new air conditioner (2020), offering added peace of mind. Ideally positioned, this home is just minutes from top-rated schools, medical facilities, shopping, dining and a short drive to the world-renowned beaches of Siesta Key. A wonderful opportunity to own a move-in-ready home in a sought-after location so schedule your private showing today.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Denise Mattmuller (941-232-8055)
1540 HILLVIEW DR, SARASOTA, FL 34239
$7,900,00087 Days on yellowkey MLS ID: A4679306
Bed: 4 Bath: 6.5 Gar: 4 Liv Area Sq Ft: 7074 Built: 2000Monthly Fee: $21 Tax: $93,548 (2024)Community: Harbor Acres Sec 2Single Family
Taxes:$93,548
Remarks: This exceptional 4-bedroom, completely renovated in 2020, highlights this waterfront estate in prestigious Harbour Acres offering 100 feet of prime Sarasota Bay frontage with private dock and lift. This masterpiece features 7074 Sq ft of living space with sweeping Bay views, a light filled open floor plan, and exceptional indoor-outdoor flow. A grand entry with dramatic staircase, opens to expansive living and dining areas, framed by floor to ceiling windows overlooking the water. The Italian modern gourmet kitchen offers premium Miele appliances, generous island seating, and a striking double sided gas fireplace shared with the living room - ideal for entertaining. This home provides rare flexibility with primary suites on both the main and upper-level levels, each with en suite baths and walk-in closet, along with additional guest suites, private office, sophisticated wine room, elevator, and dedicated fitness room. Outdoor living is a highlight, featuring a saltwater pool and spa, multiple terraces, outdoor kitchen, and professionally landscaped grounds leading to a concrete seawall and boat dock with a 30,000 pound boat lift, electric, water and fish cleaning station. Southwest exposure delivers stunning sunsets and quick access to Sarasota Bay. Spacious four-car garage complete with an electric charging station - this estate seamlessly blends opulence with modern convenience. Perfectly situated near Sarasota‘s renowned beaches, fine dining, vibrant arts scene, and top-tier medical facilities, this residence offers an unparalleled living experience in one of the most coveted waterfront communities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Fernanda Girard (941-504-4327)
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