Location: Sarasota
Keyword(s): Sarasota High
Keyword(s) High School: Sarasota High
Do Not Show Listings
300 GARDEN LN, SARASOTA, FL 34242
$2,999,000208 Days on yellowkey MLS ID: A4662830
REDUCED by $200,000 (6.3%) on 04/01/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3256 Built: 1975Monthly Fee: $10 Tax: $12,545 (2024)Community: Siesta Rev OfSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$12,545
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2024
Middle School: Brookside Middle
Remarks: A Rare Opportunity on North Siesta Key – 350 Feet of Waterfront! Discover this unique 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—is truly a boater’s and fisherman’s paradise, just steps from Shell Beach and its breathtaking sunsets. 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. All this just minutes from world-famous Siesta Key Beach, The Village shopping, dining, and nightlife, and vibrant downtown Sarasota.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Holly Parry (941-809-8050)
915 SEASIDE DR #310, SARASOTA, FL 34242
$1,399,0001 Day on yellowkey MLS ID: A4686908
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1900 Built: 2009 Tax: $14,651 (2025)Community: Siesta Key Beach Residences IiCondo
Taxes:$14,651
Tax Year: 2025
Remarks: Welcome to Unit 310 at the exclusive Hyatt Residence Club Siesta Key Beach—where elevated coastal living meets one of the most sought-after addresses on Siesta Key. Set directly on the powdery white sands of world-renowned Siesta Key Beach, this premier residence offers a rare opportunity to own within a luxury, resort-style community backed by the trusted Hyatt brand and known for its exceptional service, amenities, and strong rental demand. This beautifully updated 3-bedroom, 3-bath condominium is currently utilized as investment property and professionally managed offering a seamless, turnkey experience designed to maximize both convenience and performance. Perfectly positioned on world-famous Siesta Key Beach—consistently ranked among the top beaches in Florida, the U.S., and the world—this property benefits from steady, year-round demand for high-end vacation rentals. Whether you're seeking a dedicated income-producing asset, a future vacation retreat, or a combination of both, Unit 310 offers exceptional flexibility and long-term value. Inside, the residence features a bright, open-concept layout with three bedrooms and three full bathrooms, designed to comfortably accommodate owners and guests. Spacious living and dining areas create a welcoming environment, while the private lanai offers an additional space to relax. Residents and guests enjoy access to resort-style amenities, including a sparkling pool, fitness center, concierge services, and professional management options. With direct beach access, close proximity to Siesta Key Village, and strong, consistent rental appeal, Unit 310 presents an exceptional opportunity in the Siesta Key market. Positioned as one of the best values currently available, it is competitively priced to sell—making it an ideal choice for both investors and end users looking to capitalize on location, lifestyle, and long-term potential.
Listing is courtesy of: THE SARASOTA REAL ESTATE COMP. (941-321-5595)
Listing Agent: David Lehrman (941-321-5595)
4133 CARRIAGE DR #18, SARASOTA, FL 34241
$299,500169 Days on yellowkey MLS ID: A4668329
5 Days Off yellowkey (back on 4/1/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2000 Built: 1978 Tax: $1,713 (2024)Community: Knolls The, Bent TreeVilla
Taxes:$1,713
Elementary School: Lakeview Elementary
Middle School: Sarasota Middle
Remarks: Incredible value for a 3 bedroom, 2 bath, 2 car garage, free standing home in a condominium community with beautiful nature panorama and a family of deer who live there. Awesome views from the the living room, Florida room and primary bedroom. The current owner enclosed and central air conditioned the lanai, giving the property 2000 sq ft of living space. Vaulted ceilings with rafters in the living room and luxury vinyl flooring throughout the property with the exception of the Florida room. Guest bedrooms are generously sized. One of the few homes with nature views from living areas.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Barbara May (404-822-9264)
1789 LOMA LINDA ST, SARASOTA, FL 34239
$1,395,000516 Days on yellowkey MLS ID: A4627340
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2560 Built: 1950 Tax: $14,382 (2023)Community: Pomelo Place ResubSingle Family
Taxes:$14,382
Elementary School: Southside Elementary
Tax Year: 2023
Remarks: The West of Trail BEST BUY!! Located between Osprey Avenue and Orange Ave, rarely will you find a 2500+ square foot cement block home on an oversized corner lot (100' x 142') with 3 bedrooms, 2 bathrooms, 2 car attached garage and pool for this price. Open floor plan with high ceilings in living areas, wood flooring, spacious living and dining areas, wine cellar, separate laundry room, screened in pool and large lanai. Automatic driveway gate for garage side entry on Osprey and circular drive on Loma Linda. Prime location just down the street from popular Southside Village shops and restaurants and in highly acclaimed schoold districts. Come see for yourself and have a very pleasant surprise. No interior storm damage in the home.
4708 OCEAN BLVD #E7, SARASOTA, FL 34242
$2,350,000190 Days on yellowkey MLS ID: A4665893
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2277 Built: 1981 Tax: $16,841 (2025)Community: Windward PassageCondo
Taxes:$16,841
Remarks: Experience refined coastal living in North Siesta Key at 4708 Ocean Boulevard, a fully renovated 2025 corner residence ideally positioned on the Gulf of Mexico at Big Pass. This exceptional 3-bedroom, 3-bath condominium offers unobstructed panoramic views of the Gulf, Sarasota Bay, and distant vistas of Lido Key and downtown Sarasota. Encompassing 2,277 square feet with miles of Gulf-front views, the residence has been thoughtfully redesigned with wide-plank European engineered oak flooring, impact-rated windows and doors, and integrated smart-home technology throughout. The chef’s kitchen is a statement in both form and function, featuring custom cabinetry, Milano Dolomite countertops, a striking Macaubas Quartzite island, and premium GE Café appliances—perfect for entertaining against a backdrop of endless blue water. The primary suite is a private retreat with direct access to a Gulf-front balcony and a spa-inspired bath complete with dual vanities, rainfall shower, and bidet. Two additional guest suites provide comfort and privacy, each finished with designer details. Additional highlights include a two-car tandem garage with hurricane-rated door, new HVAC systems, electric hurricane shutters, and an integrated sound and entertainment system. Amenities include a heated pool, guest parking, and direct walking access to the sugar-white sands and vibrant Village of Siesta Key. This residence blends timeless coastal elegance with modern luxury—an extraordinary Gulf-front retreat on one of Siesta Key’s most coveted stretches of shoreline.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Stacey King (646-734-5014)
2355 BAHIA VISTA ST, SARASOTA, FL 34239
$874,983131 Days on yellowkey MLS ID: A4672605
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2086 Built: 2023 Tax: $8,758 (2024)Community: Avon Heights 2Single Family
Taxes:$8,758
Elementary School: Alta Vista Elementary
Remarks: One or more photo(s) has been virtually staged. UNRIVALED LUXURY LIVING IN PRIME SARASOTA LOCATION! Experience the epitome of luxury with this stunning custom 4 bed 2 and a half bath residential masterpiece! This immaculate two-story traditional home boasts unrivaled craftsmanship and top-tier amenities throughout. Every detail exudes sophistication, from the soaring 9’4” ceilings and elegant crown molding to the pristine wood flooring that extends throughout the home. The gourmet kitchen is an entertainer’s dream, featuring a generous island, all-wood cabinetry, and gorgeous quartz countertops. The gorgeous ground-floor master suite offers the ultimate in convenience and privacy. Indulge in the beautiful ensuite bath, featuring elegant Carrara tile flooring and a free-standing soaking tub, perfect for unwinding after a long day. Upstairs, find three generous guest bedrooms, a luxurious full bathroom, and a versatile loft area with ample storage. The bonus landing area is perfectly designed to be utilized as a dedicated open-plan office space for remote work. Constructed for superior durability and peace of mind, this home features solid block construction and an upgraded underground electric service. Enjoy the enhanced protection and natural light provided by custom PGT Florida Impact Rated windows and doors. Step outside to the expansive concrete rear lanai and embrace the true Florida lifestyle. The meticulously maintained landscaping includes lush St. Augustine grass and is effortlessly maintained by a separate irrigation meter and system. There is also room for a pool should you wish to add to the property. LOCATION, LOCATION, LOCATION! Perfectly situated to enjoy all that Sarasota has to offer. You are just minutes from the vibrant energy of Downtown Sarasota, the exclusive shopping and dining of St. Armands Circle, and the iconic shores of Lido Beach. Enjoy a short drive to world-famous Siesta Beach and the charm of Pinecraft. Exceptional proximity to top-tier medical facilities, being only half a mile to Sarasota Memorial Hospital PLUS the interstate all within 3-5 miles or just steps to public transportation. This is the exceptional lifestyle and quality home you have been waiting for!
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Rory Mcdonald (941-961-7247)
901 BEACH RD #205, SARASOTA, FL 34242
$649,00016 Days on yellowkey MLS ID: A4686468
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 753 Built: 1972 Tax: $5,156 (2025)Community: La Siesta CondominiumsCondo
Taxes:$5,156
Remarks: Welcome to the iconic La Siesta Condominiums, directly across from the main beach access of Siesta Key where coastal charm meets effortless beach days. Perfectly positioned just 100 steps from the powdery sands of Siesta Key Beach, this beautifully appointed turnkey furnished second floor condo offers breathtaking Gulf views and an unmatched connection to one of the nation’s most iconic shorelines. Designed for prime vacationing, this income producing vacation rental features an updated interior with coastal-inspired finishes including a modern kitchen, luxury vinyl plank flooring and a dining area. The primary bedroom has a king bed, secondary bedroom features two twin beds, and a queen sleeper sofa in the living room. The open-concept living space is filled with that special Siesta Key sunshine that just hits differently. You are met with a seamless flow between indoors and out featuring a hurricane rated slider door that leads you to a private balcony that becomes your front-row seat to unforgettable sunsets over the Gulf of Mexico. Ideal for both personal enjoyment and income potential, this investor-friendly property allows for up to 52 weeks of rentals annually, offering exceptional flexibility and the opportunity to maximize returns in one of Florida’s most sought-after beach destinations utilizing the professional full-time rental management program. At La Siesta, you’ll enjoy resort-style amenities including a heated pool, fitness center, clubhouse, grilling stations, on-site laundry, a covered parking space and additional storage are also included. With a seven-day rental minimum and strong demand year-round, this unit offers excellent income potential, with bookings already secured into 2026. Located just minutes from the vibrant charm of Siesta Key Village and the south bridge, you’ll have easy access taking the Siesta Key trolley to boutique shopping, waterfront dining, and experience the laid-back island nightlife. Let’s make this coastal paradise a part of your story!
Listing Agent: Ann Allen (407-949-4457)
2345 BAHIA VISTA ST, SARASOTA, FL 34239
$874,98394 Days on yellowkey MLS ID: A4672606
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2141 Built: 2023 Tax: $8,758 (2024)Community: Avon Heights 2Single Family
Remarks: One or more photo(s) has been virtually staged. New construction and under $1m in the sought after Southside school district this is very rare, but you have found it right here and your opportunity is knocking. Custom Luxury Living Near Downtown Sarasota! Welcome home to this exquisite, 4 bed 2 and a half bath custom-built residence designed by renowned Piper Navy! This two-story traditional model offers unparalleled craftsmanship and exceptional amenities just moments from Sarasota's vibrant core. Step inside to discover a truly thoughtful design, featuring soaring 9'4'' ceilings and elegant crown molding. The gourmet kitchen is a chef's dream, boasting an entertaining island, all-wood cabinetry, and stunning quartz countertops. Beautiful wood flooring flows seamlessly throughout the entire home. Constructed with block on both floors and featuring upgraded underground electric service, this residence is built for lasting quality. Enjoy peace of mind and abundant natural light thanks to custom hurricane PGT Florida Impact Rated windows and doors. The floor plan includes a gorgeous master suite on the ground floor, with a beautiful ensuite bathroom with carrara tile flooring and free standing bath to wallow the night away in after a hard day, there is also a versatile loft, with ample storage space, Upstairs is a further three guest bedrooms with luxurious bathroom and a bonus landing area that can be utlized and made into an open plan office space, should you need to work from home. Relax or entertain guests on the expansive rear concrete lanai with fenced in mature private gardens. There is also room to build a pool,should you wish to in the future The exterior is completed with an irrigation system, St. Augustine grass, and a paver front driveway, providing beautiful curb appeal.This property offers an unbeatable Sarasota lifestyle! With the boutique area of Hillview around the corner ,Siesta key beach and You are less than 5 minutes from downtown Sarasota's beautiful Marina, cultural attractions, and fine dining. Less than 10 minutes to reach the world-renowned St. Armands Circle and the pristine sands of Lido Beach, offering upscale shopping and entertainment, you are in the best central location you could ask for.
4049 SOUTHWELL WAY, SARASOTA, FL 34241
$375,00041 Days on yellowkey MLS ID: A4682640
0 Days Off yellowkey (back on 2/26/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1616 Built: 1976Monthly Fee: $27 Tax: $2,172 (2025)Community: Bent Tree VillageSingle Family
Taxes:$2,172
Remarks: Under contract-accepting backup offers. Carefree living without the condo fees & your own private pool. This 2 bedroom, 2 bath split plan home includes formal living & dining rooms, kitchen, family room, indoor laundry and lovely screened private pool area that includes outside shower. Additional feature is the oversize 2 car attached garage, all impact resistant doors & windows which should allow for maximum wind abatement insurance discounts. This property is impeccably decorated, has newer appliances and a/c unit plus tile roof with years of life remaining. Sellers are including the following items; The 54" TV and 2 decorative shelves in the family room and the island stand & room divider stand in the kitchen. Located in the popular Bent Tree Village community that is conveniently located to all of Sarasota's amenities this one of a kind single family home is one you should definitely see. Most furnishings are available.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Lisa Bouck, Pa (941-374-0165)
671 AVENIDA DEL NORTE, SARASOTA, FL 34242
$3,200,000Listed 03/31/2026 10:29PM MLS ID: A4687911
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2875 Built: 2026 Tax: $6,423 (2025)Community: Sarasota BeachSingle Family
Taxes:$6,423
Remarks: Under Construction. Custom Canal-front home underway by Salt Wave Construction, ideally located just a stroll from Siesta Key Beach and Village. Built entirely with solid block construction, this home showcases high-quality materials throughout, including hurricane-impact windows. Designed with durability in mind, its island-style construction ensures lasting strength and resilience.Thoughtfully designed to maximize its waterfront setting, the home showcases expansive porches and a spectacular rooftop deck spanning the entire roofline, offering panoramic views of the wide canal and surrounding Siesta Key landscape. This approximately 3,000-square-foot home features 4 spacious bedrooms, each with its own en-suite bath, delivering both comfort and privacy. The primary suite is a true retreat, boasting a luxurious oversized bathroom, an expansive walk-in closet, and a private canal view loggia with a fireplace—perfect for relaxing evenings. Crafted with a seamless blend of sophisticated design and high-quality finishes, this residence provides an unparalleled sanctuary. The outdoor living space includes an open pool area, ideal for entertaining, unwinding, or enjoying direct access to Sarasota’s scenic waterways. Located just minutes from world-renowned white sand beaches, vibrant dining, shopping, and entertainment, this home perfectly balances tranquility and convenience in one of Sarasota’s most desirable neighborhoods. Estimated completion: approximately 10-12 months.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Jessica Hoffman (941-400-5778)
339 TREASURE BOAT WAY, SARASOTA, FL 34242
$3,000,0001 Day on yellowkey MLS ID: A4685922
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2689 Built: 1957 Tax: $16,361 (2025)Community: Harmony SubSingle Family
Taxes:$16,361
Remarks: Elegant Siesta Key Waterfront Living. Don’t just move. Arrive! Enter into your residence, and the world falls away. Picture-perfect postcard views from nearly every room await to welcome you home. Nestled on an unrivaled point at the intersection of the Grand Canal’s most impressive waterways, this newly renovated, rare find offers you the complete package. Luxury finishes, high-tech resilience, and the quintessential Siesta Key lifestyle are prepared for you to move in ready. A brief stroll from the vibrant energy of Siesta Key Village and the quartz sands of Siesta Beach. With an astounding approximately 240 feet of private seawall and offering long-range canal views creating a lagoon-like setting, this opportunity simply cannot be replicated. While offering crisp, clean lines of modern contemporary style, the infrastructure is strictly 2026-ready. This unique residence provides both luxurious aesthetic appeals, featuring a fully updated chef’s kitchen and designer baths, and "invisible luxury". The peace of mind that comes from the resilience of a durable metal roof, new seawall, and all-new high-velocity hurricane windows and doors, new flooring, wood burning fireplace, and new electrical, plumbing, as well as new three-zone HVAC and mechanical systems, has been thoughtfully provided. And, for your peace of mind, professional night vision high-tech security cameras and systems were installed in 2026. The preferred split plan offers three additional bedrooms, including a private guest suite with its own separate entrance and ensuite bath. Life at 339 Treasure Boat Way centers around the water. Venture out onto the paved, open-air pool deck to find a 2026 freshly re-finished Aqualink-controlled, saltwater, heated pool and spa with LED lighting. Enjoy gentle, golden morning sun and cool, shaded afternoons—perfect for entertaining and alfresco dining. An oversized detached two-car air-conditioned garage, fenced yard for pets, and ample guest parking.
Listing is courtesy of: COLDWELL BANKER REALTY (941-739-6777)
Listing Agent: Tonna Gruber (941-232-8950)
19 WHISPERING SANDS DR #302, SARASOTA, FL 34242
$1,350,0001 Day on yellowkey MLS ID: A4685512
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1464 Built: 1973 Tax: $6,561 (2025)Community: Whispering Sands Sec 7Condo
Taxes:$6,561
Remarks: Experience the ultimate beachfront lifestyle in this stunning two-bedroom, two-bathroom condo that's been completely renovated with fresh style and modern touches. With 1,464 square feet of thoughtfully designed living space, this home offers breathtaking full views of the Gulf of Mexico and pristine beach right outside your door. Step inside to discover a bright, open layout that maximizes both comfort and those incredible water views. The recent renovation means everything feels brand new, from the sleek finishes to the updated amenities throughout. Both bedrooms are generously sized, including a spacious primary bedroom that serves as your personal retreat after days spent soaking up the Florida sunshine. The location puts you in the heart of Siesta Key's most desirable area, just steps from the famous powdery white sand beach that draws visitors from around the world. When you're ready to explore, Siesta Key Village is practically at your doorstep, offering an amazing collection of restaurants, shops, and entertainment options. Whether you're craving fresh seafood, tropical drinks, or just shop, the village has something for everyone. The building features a huge community pool perfect for lazy afternoons when you want a break from the beach. For daily needs, Morton's Siesta Market is conveniently nearby, and Boyd Park offers additional outdoor recreation options.
Listing is courtesy of: SARASOTA REALTY CENTER LLC (941-702-3635)
Listing Agent: Frank Golio Jr., Pllc (941-363-1075)
1500 STATE ST #603, SARASOTA, FL 34236
$579,0001 Day on yellowkey MLS ID: A4688177
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 736 Built: 2017 Tax: $7,206 (2025)Community: 1500 State StreetCondo
Taxes:$7,206
Middle School: Booker Middle
Remarks: LOCATION, LOCATION, LOCATION! This charming, furnished boutique penthouse is one of the most uniquely positioned modern residences in the heart of downtown Sarasota. Ideally located at the corner of State Street and Lemon Avenue, it offers captivating bird’s-eye views of the bay and an unmatched urban setting. The residence features a well-designed living and dining area, a functional kitchen, a generously sized bathroom, and a bright, airy bedroom with built-in closets. Step outside your door and enjoy immediate access to Sarasota’s premier dining, theaters, comedy clubs, art scene, and vibrant nightlife—all conveniently located. Whether you’re seeking a stylish downtown retreat or a strong investment opportunity, this property delivers. Currently leased at $3,900 per month, it offers immediate income potential.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-907-2000)
Listing Agent: Elsie Salazar (941-284-7645)
1647 SIESTA DR, SARASOTA, FL 34239
$1,690,0001 Day on yellowkey MLS ID: A4684901
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3032 Built: 2025 Tax: $17,778 (2025)Community: BayviewSingle Family
Taxes:$17,778
Remarks: Welcome to this stunning coastal home with elevator, featuring 5 bedrooms, 2.5 bathrooms, and 3,023 square feet of living space. Additional opportunity to add bathrooms with modification add-on with the builder. From the moment you enter, you'll be captivated by the open floor plan, pool view, and fantastic design. This dazzling property, boasts an open floor plan that features high ceilings, natural light, and high-quality finishes throughout. The home features a modern and elegant kitchen with top-of-the-line Cafe' appliances, quartz countertops, and custom cabinetry. The primary bedroom located on the upper level can be accessed by elevator is a true sanctuary, offering a plush and peaceful retreat. It boasts vaulted ceilings, en-suite bathroom that includes a soaking tub and a separate shower that's great for unwinding after a long day. The room also features a generously sized walk-in closet with abundant space for storage and organization as well as a private terrace. On the second floor you will find three vast bedrooms, with plenty of closet space for added convenience and comfort. One of the most notable features of the second floor is the sizable sundeck and balcony, which are attached to both bedrooms. The laundry room is conveniently located on the second floor as well. The spacious bonus room offers endless possibilities, from an office, den, playroom, media center or a home gym. This home has two patios with an outdoor area with a large pool and hot tub that seamlessly blend the indoor and outdoor living with meticulously planned landscaping. Situated between Siesta Key and Downtown Sarasota, you will have easy access to some of the best beaches, restaurants, and shopping in the area. Whether you are looking for a day at the beach, a night out on the town, or a quiet evening at home, this home has everything you need.
Listing is courtesy of: PHAM REALTY GROUP LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
3424 OLD OAK DR, SARASOTA, FL 34239
$1,195,0001 Day on yellowkey MLS ID: A4688216
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1368 Built: 1953 Tax: $10,828 (2025)Community: Shoreland WoodsSingle Family
Taxes:$10,828
Remarks: Craving a low-maintenance, island-inspired lifestyle just moments from sparkling open water, world-famous beaches, and Sarasota’s most coveted destinations? This quaint Florida bungalow located in west of trail delivers the perfect blend of charm, location, and effortless living—just minutes to Siesta Key and steps from the coastal lifestyle you’ve been dreaming of. Tucked away in one of Sarasota’s most desirable “West of the Trail” neighborhoods, 3424 Old Oak Dr has been thoughtfully redesigned to preserve its original character while introducing timeless, modern updates. From the moment you arrive, the lush tropical landscaping, winding garden paths, and private courtyard-style entry create a warm, inviting ambiance that feels like your own hidden oasis. Inside, the home showcases a light-filled, airy design highlighted by vaulted wood-beam ceilings, soft coastal tones, and an open-concept layout that seamlessly blends comfort and style. The beautifully updated kitchen features granite countertops, open shelving, stainless steel appliances, and designer finishes, creating a space that is both functional and visually stunning. The living area centers around a charming wood-burning fireplace, adding warmth and character, while French doors invite natural light and connect indoor and outdoor living spaces effortlessly. The home offers flexible living spaces ideal for a primary residence, seasonal retreat, or income-producing property. Each room reflects a curated, coastal aesthetic with tasteful updates while maintaining the home’s unique bungalow charm. Step outside to your private backyard sanctuary, where a screened-in heated pool is surrounded by mature tropical landscaping, creating a serene and secluded environment perfect for relaxing or entertaining. An outdoor shower adds to the coastal lifestyle experience, while multiple seating areas and garden spaces enhance the home’s tranquil, resort-like feel. Located just minutes from Siesta Key Beach, Southside Village, downtown Sarasota, Sarasota Memorial Hospital, and top-rated dining and shopping, this home offers unmatched convenience paired with a laid-back coastal lifestyle. Rarely does a property combine location, charm, income potential, and lifestyle so seamlessly. This is your opportunity to own a truly special Sarasota bungalow where every day feels like a vacation.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Adnan Dedic (941-726-2917)
838 NORSOTA WAY, SARASOTA, FL 34242
$4,190,0001 Day on yellowkey MLS ID: A4688144
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 3001 Built: 2026 Tax: $11,779 (2025)Community: Bay IslandSingle Family
Taxes:$11,779
Remarks: Pre-Construction. To be built. Discover timeless coastal elegance in this upcoming traditional-style new construction home, perfectly situated in the highly coveted Bay Island neighborhood on Siesta Key. Designed to blend modern sophistication with classic charm, this residence offers an extraordinary lifestyle of luxury and tranquility. Set on a 13,815 sqft. homesite, this 3,001 sqft. masterpiece features 5 spacious bedrooms, 5 full bathrooms, 2 half baths, and an office. There is opportunity for a private fitness studio, and there are 3 garage spaces. Thoughtfully curated interiors showcase refined finishes, soaring ceilings, and abundant natural light that capture lush landscaping views throughout. At the heart of the home lies a gourmet chef’s kitchen—a showpiece of design and functionality. A striking quartz waterfall island anchors the open-concept layout, framed by elegant pendant lighting, custom cabinetry, and top-of-the-line stainless steel appliances. Perfectly suited for entertaining or relaxed coastal living, the adjoining living and dining areas flow seamlessly to the outdoors. Step into your private tropical retreat, where a resort-style pool with a champagne spa is surrounded by lush landscaping and swaying palms. Host the family or guests with the covered outdoor kitchen and the dinning space. The outdoor living space is designed for serenity and sophistication, offering the ideal backdrop for gatherings or quiet moments alike. Located in one of Sarasota’s most desirable neighborhoods, this remarkable new construction home offers privacy, convenience, and effortless access to world-class beaches, fine dining, and vibrant cultural attractions. A rare opportunity to own a brand-new luxury residence on Bay Island—where coastal beauty meets timeless design.
5010 LAHAINA DR, SARASOTA, FL 34232
$579,90076 Days on yellowkey MLS ID: A4678105
Bed: 4 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 2333 Built: 1960 Tax: $2,564 (2025)Community: Ridgewood Estates ResubSingle Family
Taxes:$2,564
Elementary School: Brentwood Elementary
Middle School: McIntosh Middle
Remarks: One or more photo(s) has been virtually staged. Experience modern Florida living in this beautifully renovated residence featuring a serene pool-side oasis with a versatile detached guest house. Highlighted by a refined chef's kitchen, this home feels newly built. Sparkling pool with therapeutic jets and seating for six sets the tone for resort style relaxation. Detached guest/pool house offers complete independence for visiting friends, extended family or potential rental opprotunities. Convient location just minutes to Sarasota's top beaches, dinning and attractions, this property blends confort, elegance and unmatched convenience. Plenty of parking for all, bring your RV, Boat, etc., behind fence parking available, parking pads, two driveways and a garage. No Association, only county restrictions apply.
Listing is courtesy of: SWILLEY & ASSOCIATES REALTY (941-504-0947)
Listing Agent: Regina Swilley (941-504-0947)
1732 SHORELAND DR, SARASOTA, FL 34239
$1,995,00046 Days on yellowkey MLS ID: A4682616
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3790 Built: 2018 Tax: $20,697 (2025)Community: Shoreland Woods SubSingle Family
Taxes:$20,697
Remarks: Welcome to modern West of Trail living — where space, style, and location come together in one of Sarasota’s most desirable family neighborhoods. Designed for the buyer who wants room to grow without sacrificing lifestyle or convenience, this stunning newer construction home offers the perfect balance of luxury, functionality, and everyday ease. From the moment you arrive, the quiet, tree-lined streets and classic white-picket-fence charm of the neighborhood set the tone. Surrounded by multi-million-dollar homes and a true community feel, this is the kind of place where families ride bikes in the evenings, walk to school, and enjoy a relaxed yet refined Sarasota lifestyle. Step through the front door and into a dramatic, light-filled foyer that immediately showcases the home’s modern aesthetic and open, airy design. Soaring ceilings, sleek lines, and expansive glass create a sense of volume and energy, while the open-concept floor plan delivers the flexibility today’s families need. The main living space flows effortlessly into a designer kitchen featuring an oversized island, premium appliances, custom cabinetry, and abundant storage — ideal for casual family dinners or entertaining friends. With five bedrooms plus a dedicated office and a spacious bonus room/loft, this home was designed around real life. Whether you need guest space, a media room, playroom, or homework zone, there is room for everyone to spread out while still feeling connected. One of the most unique features is the flexibility of having a choice of a primary suite on the first or second floor, making the home ideal for multi-generational living, long-term flexibility, or simply choosing the layout that best fits your lifestyle. Outside, the lifestyle continues. The heated pool and outdoor kitchen create an effortless indoor-outdoor flow perfect for weekend gatherings or quiet evenings at home. Unlike many tropical properties, the landscaping is intentionally low-maintenance, giving you the beauty of a resort-style setting without endless upkeep — more time enjoying, less time working. Built above the flood plain, this home offers an important advantage for peace of mind and long-term savings: no flood insurance required. Modern construction standards, quality materials, and hurricane-rated features ensure durability and efficiency for years to come. Location is everything, and this one is hard to beat. Walk to highly rated Southside Elementary and the boutiques and restaurants of Southside Village. Enjoy dinner just a block away at some of Sarasota’s most loved restaurants. Spend your weekends at Siesta Key Beach or downtown Sarasota — both just about eight minutes away — then return home to a quiet, suburban setting that feels private, safe, and unmistakably family-friendly. This is more than just a beautiful modern home — it’s a lifestyle designed around space, comfort, and connection in one of Sarasota’s most coveted neighborhoods. If you’ve been searching for a move-in-ready home with bedrooms to spare, a pool, modern design, and a location that checks every box, this is the one. Schedule your private showing and experience West of Trail living at its best.
Listing is courtesy of: EXP REALTY LLC (800-486-1794)
Listing Agent: Mark Coppens (941-444-0436)
3512 CAMINO REAL, SARASOTA, FL 34239
$2,745,000145 Days on yellowkey MLS ID: A4671290
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3810 Built: 2025 Tax: $6,583 (2025)Community: GranadaSingle 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.
4375 SEDLEY LN, SARASOTA, FL 34241
$750,00019 Days on yellowkey MLS ID: A4686157
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2615 Built: 1980Monthly Fee: $27 Tax: $4,228 (2025)Community: Bent Tree VillageSingle Family
Taxes:$4,228
Remarks: One or more photo(s) has been virtually staged. Updated interior photos as of 03/31/2026. Welcome to this beautifully maintained 3-bedroom, 3.5-bath pool home with a 3-car garage, offering 2,615 square feet of comfortable living in the highly desirable Bent Tree Village community. Perfectly situated at the end of a quiet cul-de-sac with virtually no through traffic, this home enjoys an exceptionally peaceful and private setting rarely found in the neighborhood. Surrounded by mature landscaping and overlooking serene creek and golf course views, the property offers a truly picturesque backdrop, creating a calm and inviting atmosphere both inside and out. Designed for comfortable living and entertaining, the home features spacious living and family rooms along with a large kitchen highlighted by vaulted ceilings, rich cherry cabinetry, stone countertops, stainless steel appliances, a built-in oven and microwave, separate cooktop, and a convenient pass-through window to the outdoor patio. The split-bedroom floor plan provides excellent privacy for both owners and guests, while a cozy wood-burning fireplace and east-facing exposure fill the home with warm natural light throughout the day. Step outside to the private screened lanai and pool area, where the tranquil water and golf course views create an ideal setting for relaxing, entertaining, or simply enjoying the quiet natural surroundings. Numerous updates provide peace of mind, including a 2015 roof, 2022 HVAC system, 2021 water heater, 2016 pool resurfacing, 2019 poly-pebble patio, 2022 irrigation system, 2021 hurricane shutters, and a 2017 garage door. Conveniently located near I-75, University Town Center, SRQ International Airport, Gulf beaches, Mote Marine SEA, Rothenbach Park, Urfer Family Park, and numerous golf courses, this home offers the perfect balance of privacy, scenery, and convenience—all within one of Sarasota’s most established communities.
Listing is courtesy of: MEDWAY REALTY (941-375-2456)
Listing Agent: Alex Morel Pa (941-376-4580)
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