Location: Sarasota
Do Not Show Listings
4926 PRESTON WAY, SARASOTA, FL 34232
$449,90027 Days on yellowkey MLS ID: A4694417
1 Days Off yellowkey (back on 5/27/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1552 Built: 1986 Tax: $3,475 (2025)Community: Cedar Hollow Unit 3Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,475
Elementary School: Fruitville Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: McIntosh Middle
Remarks: Under contract-accepting backup offers. Home is that special place where comfort is found and memories are made. This beautifully updated residence in one of Sarasota’s convenient, established neighborhoods—with spacious lots, and a true sense of community. BE SURE TO CHECK OUT THE VIRTUAL TOUR. No HOA restrictions mean this home offers the freedom to truly make it your own, whether enjoying outdoor gatherings or hooking up the boat for a well-deserved weekend of relaxation on the bay and Gulf waters that Sarasota is known for. Proximity to top-rated schools, everyday shopping and dining, major roadways, and world-class Gulf beaches make daily life effortless while staying connected to everything Sarasota has to offer. Discover why homes in Cedar Hollow do not typically last long. This inviting single-family home, situated on a corner lot, offers approximately 1,552 square feet of thoughtfully designed living space, featuring high ceilings, three bedrooms, two bathrooms, and a versatile bonus room ideal for a home office, hobby area, or flexible living. Fresh updates throughout create a move-in-ready home, so weekends aren’t spent on repairs. If an outdoor shop or accessory building is in your plans, there is plenty of room for a bold plan, and the corner lot is perfect for secondary access. Privacy is usually high on buyers’ priority lists of “must have” items, so the dead end that just a short distance beyond is a definite plus. Inside, the open, light-filled layout showcases beautiful tile flooring in the main living areas (updated 2020) and new vinyl flooring in the bedrooms (2025). The heart of the home is the spacious kitchen, equipped with brand-new Samsung Bespoke appliances (2025), elegant granite countertops, rich wood cabinetry, and a functional island—perfect for casual meals and entertaining. Adjacent dining and living spaces flow seamlessly. The primary bedroom serves as a peaceful retreat, while the additional bedrooms offer flexibility for family, guests, or personal use. Updated bathrooms provide everyday convenience and contemporary finishes. Step outside to enjoy Florida living at its finest: a fully vinyl-fenced backyard (2024) with fresh landscaping (2025), plus a spacious 10x16 permitted shed complete with insulation and air conditioning—ideal for storage, a workshop, or a private escape. Additional recent enhancements include hurricane-impact windows and doors (2019), a newer roof (2022), an HVAC system (2021), a water heater (2021), a reverse osmosis water system (2024), a freshly painted exterior (2025), an updated garage door opener (2025), and new gutters (2025). A one-car garage and ample parking complete the practical appeal. Siesta Key beach is just 15 minutes away. The interstate, UTC Mall, Benderson Park, along with all the shopping, and an endless selection of dining options, are all within 10 minutes. This residence stands out for its thoughtful updates, low-maintenance design, and unbeatable location in a vibrant Sarasota community. A wonderful opportunity for comfortable, worry-free living in a highly desirable area. Schedule your private showing today!
Listing is courtesy of: SARASOTA REAL ESTATE GROUP (941-922-8400)
Listing Agent: John Woodward (941-922-8400)
4735 WOODBROOK DR, SARASOTA, FL 34243
$329,90034 Days on yellowkey MLS ID: A4693683
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1080 Built: 2012Monthly Fee: $179 Tax: $4,024 (2025)Community: Woodbrook Ph ISingle Family
Taxes:$4,024
Elementary School: Robert E Willis Elementary
High School: Braden River High
Middle School: Braden River Middle
Remarks: Welcome to this beautiful 2-bedroom, 2-bathroom single-family home with a 2-car garage in the highly desirable gated Woodbrook community of Sarasota, FL 34243. Offering 1,080 square feet of thoughtfully designed living space, this move-in ready home combines modern upgrades, comfort, and low-maintenance Florida living in an unbeatable Sarasota location near University Town Center (UTC).Inside, you’ll find a bright open-concept floor plan filled with natural light, spacious living and dining areas, and a well-appointed kitchen ideal for both everyday living and entertaining. Recent upgrades include a brand-new AC system (2026) and brand-new luxury vinyl plank flooring throughout the home, with tile flooring in both bathrooms for added durability and style. The private primary suite features an en-suite bathroom and generous closet space, while the split-bedroom layout offers flexibility for guests, family, or a home office.Enjoy peaceful outdoor living in a beautifully maintained gated neighborhood featuring a community pool and playground, perfect for enjoying the Florida lifestyle year-round. Located in Flood Zone X, this property offers added peace of mind with low flood risk.Ideally located just minutes from UTC shopping and dining, Nathan Benderson Park, Sarasota-Bradenton International Airport, downtown Sarasota, Lakewood Ranch, and the world-famous Gulf Coast beaches including Siesta Key and Lido Key. With convenient access to I-75, this home places shopping, restaurants, golf, entertainment, and top Sarasota attractions right at your fingertips.Whether you’re searching for a primary residence, seasonal retreat, retirement home, or investment property in Sarasota, this Woodbrook home offers exceptional value in one of Sarasota’s most convenient and desirable 34243 communities.
Listing is courtesy of: MOUNT VERNON PROPERTY MGMT INC (941-957-4663)
Listing Agent: Jennifer Herman (941-957-4663)
3538 65TH AVENUE CIR E, SARASOTA, FL 34243
$339,900320 Days on yellowkey MLS ID: TB8391530
REDUCED by $5,000 (1.4%) on 05/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1217 Built: 1988Monthly Fee: $29 Tax: $4,150 (2024)Community: Centre LakeSingle Family
Taxes:$4,150
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Check out this 3 bedroom 2 bath 2 car garage home in Centre Lake. Great water views from nearly every room adds to the quiet enjoyment of this home. All remodeled with a large living room and an open kitchen as well a split plan layout and a master bedroom/master bath. A 2 car garage and many updates throughout enhance this home. Close to all the activities of Sarasota and Bradenton. Come chek it out.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Dave Liddle (727-422-2564)
2902 CAPTIVA GARDENS DR #3, SARASOTA, FL 34231
$259,90040 Days on yellowkey MLS ID: A4692905
REDUCED by $20,000 (7.1%) on 05/24/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1206 Built: 1975Monthly Fee: $621 Tax: $2,243 (2025)Community: Captiva GardensSpa: NoVilla
Taxes:$2,243
Elementary School: Gulf Gate Elementary
High School: Riverview High
Middle School: Brookside Middle
Remarks: Looking for a Value Priced "Updated" Villa in Captiva Gardens with or without furniture? You've found it! All of these updates within the last 3 years: Luxury Vinyl Flooring*Hurricane Windows*Kitchen Appliances*Interior Freshly Painted*Walk-in Tub/Shower*LG Washer all in on*Recessed lighting & More! This villa has Coastal Fixtures and Decor and the furniture is optional! The layout is wonderful with two distinct living areas, providing ample space for relaxation and entertainment. Beautiful shell landscaping with decorative pots and a Lanai with a brick patio, which is a great place to unwind. Residents have full access to the Pool and the well maintained Clubhouse that is perfect for events and social gatherings with all of the friendly neighbors. The pool offers a refreshing escape and is ideal for soaking up the Florida sun or doing a leisurely swim. The location of this community is superb and it is within minutes to World Renowned Siesta Key Beaches, Gulf Gate Library, Legacy Trail, Gulf Gate Shops and Restaurants, Several Fitness Centers, A+ Schools and Shopping. UTC Mall is only 20 minutes away, as well as cultural downtown Sarasota with great nightlife, fine restaurants, opera, movie theaters and more. The one car garage is an added bonus that provides not only parking convenience but also adds additional storage options. You'll love living in sought-after South Sarasota. Whether you want to explore local parks, shop, hop on over to Siesta Key or take a walk or bike ride ... South Sarasota always has something to do. Make this one yours but don't wait!
Listing is courtesy of: DEBBIE HERING REALTY & ASSOC. (941-320-1070)
Listing Agent: Debbie Hering (941-320-1070)
7755 PINE TRACE DR #7755, SARASOTA, FL 34243
$379,90058 Days on yellowkey MLS ID: A4690016
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1605 Built: 1988 Tax: $4,683 (2025)Community: Pine TraceVilla
Taxes:$4,683
Elementary School: Kinnan Elementary
Remarks: Fully Furnished | Turnkey Living in Palm Aire's Pine Trace. Welcome to 7755 Pine Trace Drive a beautifully maintained, fully furnished 3-bedroom, 2-bathroom residence offering 1,605 square feet of effortless Florida living in one of Sarasota's most desirable communities. Step inside to an open-concept living area that's move-in ready and thoughtfully appointed for both everyday comfort and easy entertaining. The modern kitchen features contemporary appliances and generous counter space ideal for anyone who loves to cook and gather. Three well-sized bedrooms provide private retreats for family or guests, and the attached 2-car garage delivers both secure parking and valuable storage. Extensively Updated in 2024: New A/C, refrigerator, stove, microwave, garbage disposal, garage door, washer, dryer, lighting, ceiling fans, blinds, and a brand-new steam room in the pool area. Roof replaced in 2021. This home has been meticulously cared for buy with confidence. The Pine Trace Community offers a tranquil, beautifully landscaped setting with a friendly neighborhood feel. Nearby Palm Aire Country Club is a private, member-owned equity club featuring golf, tennis, padel, pickleball, visual arts programming, food and wine events, gardening groups, and active social card clubs. Four equity membership options are available. Location is everything. Minutes from University Town Center with 100+ specialty stores and 20+ restaurants. Easy access to downtown Sarasota's acclaimed dining scene, Sarasota Opera House, and world-class cultural destinations including The Ringling Museum. Beach days are just a short drive to Lido Key's white sand shores, St. Armands Circle shopping and dining, or legendary Siesta Beach consistently ranked among the best beaches in the country. Comfort, convenience, and the best of the Sarasota lifestyle all waiting for you at Pine Trace.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Brandy Loebker (941-404-4737)
526 N SPOONBILL DR, SARASOTA, FL 34236
$8,800,000189 Days on yellowkey MLS ID: A4674712
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 5287 Built: 2026Monthly Fee: $89 Tax: $10,057 (2024)Community: Bird Key SubSpa: YesSingle Family
Taxes:$10,057
Remarks: One or more photo(s) has been virtually staged. Under Construction. Welcome to a rare opportunity on iconic Bird Key—an exquisite, Fortified Gold Standard residence masterfully crafted by Dynan Construction, Sarasota’s premier luxury builder. This architectural masterpiece seamlessly blends elevated coastal design with structural integrity, refined interiors, and resort-level amenities across 5,287 sq. ft. of sprawling interior living space. From the moment you enter, every detail speaks of thoughtful craftsmanship and timeless luxury. A private elevator offers effortless access to all levels, while an impressive glass-enclosed wine room serves as a sculptural centerpiece—perfect for showcasing your collection. Step outside to your private resort—an extraordinary resort-style pool and grotto spa designed to extend your interior living experience into a true outdoor sanctuary. The custom pool features oversized sun-shelf, cascading water features, ambient LED lighting, and integrated seating areas, all crafted to mirror the luxury of a five-star coastal retreat. Tucked beneath natural stone formations, the grotto spa offers a sheltered, tranquil escape with spa jets, mood lighting, and a cave-like ambiance that elevates relaxation to an art form. The home’s open-concept floor plan flows with intentionality, allowing natural light to fill each room while preserving privacy and warmth. Expansive living and dining spaces overlook lushly curated grounds, enhanced by a premium landscape package featuring mature palms, tropical botanicals, and tranquil outdoor living zones ideal for year-round enjoyment. Built to the highest standards, this residence is certified Fortified Gold, delivering unmatched resilience, superior engineering, and long-term protection—setting a new benchmark for luxury coastal construction on Bird Key. Located in one of Sarasota’s most exclusive waterfront communities, this home places you at the center of everything Sarasota is celebrated for. A short stroll or bike ride brings you to the newly reimagined 2026 Bird Key Yacht Club, offering world-class dining, boating, fitness, and social amenities. Minutes away are the white-sand shores of Lido Beach, the boutique shopping and dining of St. Armands Circle, and the vibrant arts and cultural scene of downtown Sarasota—including the Sarasota Opera, Asolo Repertory Theatre, Marie Selby Botanical Gardens, and The Ringling Museum. Bird Key is more than a neighborhood—it’s a lifestyle defined by elegance, prestige, and convenience. This exceptional Dynan-built estate presents a rare opportunity to own a home where luxury, craftsmanship, and location converge.
Listing is courtesy of: COASTAL RESERVE (941-586-7736)
Listing Agent: Cassandra Miller (941-586-7736)
1771 RINGLING BLVD #703, SARASOTA, FL 34236
$648,900322 Days on yellowkey MLS ID: A4658164
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1440 Built: 2006 Tax: $8,759 (2024)Community: Rivo At RinglingSpa: YesCondo
Taxes:$8,759
Elementary School: Southside Elementary
Middle School: Booker Middle
Remarks: One or more photo(s) has been virtually staged. Offering an unmatched combination of structural peace of mind, a walk-to-everything downtown lifestyle, and rare perks like two secure parking spaces, this meticulously updated residence represents the ultimate value play in Sarasota’s luxury market and demands an in-person tour. DOWNTOWN VALUE & PRIME LOCATION | 2-BR + DEN | SECURE MODERN CONSTRUCTION For the buyer seeking the perfect intersection of strong value, a walk-to-everything location, and the structural integrity of a newer building, Residence #703 at Rivo at Ringling delivers on every front. Built in 2006, this 16-story contemporary tower stands out in downtown Sarasota for its modern concrete construction, excellent building health, and a fully funded reserve—offering rare peace of mind and long-term financial security. Encompassing just 106 residences around a dramatic, light-filled central atrium, Rivo offers an intimate, well-managed community feel with lower fees and better value per square foot than surrounding new construction, all while placing you steps from the city's best dining, theater, and waterfront. Inside, this meticulously updated 2-bedroom plus den, 2-bathroom residence offers an effortless, move-in-ready transition with both bedroom sets fully included in the sale. The bright, open-concept floor plan features a freshly modernized chef’s kitchen with sleek quartz countertops, a full-height seamless backsplash, custom stacked cabinetry, and stainless steel appliances. Expanses of glass open to an impressive, oversized 20x9-foot north-facing terrace, extending your living space outdoors for alfresco dining against a backdrop of the city skyline and a glimpse of Sarasota Bay. This split-bedroom layout ensures maximum privacy for guests, while the flexible custom den easily functions as a home office, media room, or a third sleeping space. Serving as a quiet retreat, the primary ensuite is complete with direct terrace access, a large walk-in closet, and a spa-inspired ensuite bathroom featuring a frameless glass shower and premium modern finishes. Practical efficiency and convenience are woven throughout the property, from the interior peace of an exterior-facing AC closet with a UV air-purifying system to a wealth of rare downtown parking assets. This residence includes an exceptionally rare commodity in downtown living - two oversized, under-building parking spaces in a secure gated garage! Also included is a private storage room, secure bike and kayak storage, and available EV charging stations. Rivo at Ringling further elevates its value proposition with resort-style amenities, including concierge services, a heated pool and spa with a sun deck, a covered grilling terrace, a state-of-the-art fitness center, and a pet-friendly policy with flexible rental guidelines. Combining a high-quality newer build, fully funded financial health, and a partially furnished (bedrooms only) head start in the heart of downtown, this residence represents an unmatched value play in Sarasota’s luxury market. Easy to view and easier to fall in love with Rivo and this 7th floor property.
Listing is courtesy of: CORCORAN DWELLINGS REALTY (941-200-4663)
Listing Agent: Shayla Twit (941-544-7690)
10844 ECLIPSE ST, SARASOTA, FL 34241
$564,65162 Days on yellowkey MLS ID: A4690301
INCREASED by $25,000 (4.6%) on 05/01/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1790 Built: 2026Monthly Fee: $251Community: Cassia At Skye RanchSpa: NoSingle Family
Taxes:$0
Remarks: Under Construction. What's Special: Pond View | No Rear Neighbors | Convenient 1st Floor Living. New Construction - December Completion! Built by America's Most Trusted Home Builder. Welcome to the Saint Vincent at 10844 Eclipse Street in Cassia at Skye Ranch! This thoughtfully designed new home embraces easy Florida living with a welcoming foyer that includes a convenient powder room and leads you straight into the heart of the home. The kitchen overlooks the dining area and great room and features quartz countertops, an apron front kitchen sink, soft close cabinets, and a layout that flows perfectly for everyday living. Sliding doors open to the covered lanai, creating a bright and comfortable connection between indoor and outdoor spaces. Tucked at the back of the home, the primary suite offers a relaxing retreat with an en-suite bath and a spacious walk-in closet, while two secondary bedrooms share a full bathroom and a dedicated study adds flexible space. Whole house impact windows provide added peace of mind, and the laundry room offers direct access to the two-car garage. Skye Ranch sits in a prime Sarasota location at Clark and Lorraine Roads, offering a vibrant setting with access to the Skye Ranch K-8 school. The community preserves natural beauty with grand oaks, palms, wetlands, lakes, and native wildlife. Miles of trails connect you to nature, parks, and exceptional on-site amenities. Additional Highlights Include: Study in place of flex, 8' interior doors, tray ceiling pkg, impact windows, pre-plumb for future laundry tub, and upgraded cabinets and flooring. Photos are for representative purposes only. MLS#A4690301
Listing is courtesy of: TAYLOR MORRISON RLTY OF FLA (866-495-6006)
Listing Agent: Michelle Campbell (866-495-6006)
2153 PUEBLO CIR #V14, SARASOTA, FL 34231
$199,000141 Days on yellowkey MLS ID: A4679111
REDUCED by $33,000 (14.2%) on 05/27/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1008 Built: 1972 Tax: $2,363 (2025)Community: Woodside Village WestSpa: NoCondo
Taxes:$2,363
Remarks: Located in the heart of Sarasota, this ground floor 2/2 villa is very comfortable, manageable and private. Tucked away in a private courtyard, this villa has been lovingly maintained and upgraded by its owner. The windows and sliding glass door were replaced in 2016 with PGT vinyl frame impact double hung windows and impact sliding glass in the sliding door. The HVAC unit was replaced in 2022. The interior of the entire villa was freshly painted in 2022. The kitchen has cabinets galore and plenty of counter space. The laundry closet has a washer and dryer and storage space. The side door in the kitchen and the slider in the dining area lead to the private patio in the back of the villa. With permission from the Association, this patio can be screened in. There is a large walk in the closet off of the primary bedroom plus an ensuite bath with a large vanity and a step-in shower. Grab bars have already been installed in the shower. There is a full guest bath with tub/shower. More closet space and storage in the second bedroom plus in the large hallway closet. This active 55+ community has a swimming pool. Each unit has its own parking space plus guest spots. There are a total of 48 units in this private enclave. Conveniently located close to shopping, restaurants, medical offices and houses of worship plus only a few miles away from America's #1 Beach at Siesta Key. Being sold turnkey furnished, this villa is move in ready.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Helene Hyland (941-685-2274)
3953 PRAIRIE DUNES DR, SARASOTA, FL 34238
$960,00071 Days on yellowkey MLS ID: A4689054
REDUCED by $15,000 (1.5%) on 04/19/2026
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3182 Built: 1985Monthly Fee: $125 Tax: $6,809 (2025)Community: Country Club Of Sarasota TheSpa: YesSingle Family
Taxes:$6,809
Middle School: Sarasota Middle
Remarks: Welcome to 3953 Prairie Dune Drive, located in the gated Country Club of Sarasota with a fully staffed security gate providing twenty-four-hour access control. Positioned along the second fairway, this five-bedroom, four-bathroom home offers golf course views and updates, including a new roof and replumbing. Low HOA fees add to long-term value, while the layout and setting provide an opportunity for updates or personalization over time. The interior features high ceilings, natural light, and a functional floor plan with two separate living areas. The formal dining room with a bay window sits adjacent to the family room with a wet bar. The kitchen includes a breakfast area, large pantry closet, wood cabinetry, bar seating, center cooking island, and pass through window to the lanai and pool area. The upstairs primary suite includes three closets, dual vanities with a separate makeup station, soaking tub, walk-in shower, and a loft overlooking the main living area and fairway. With five bedrooms, four bathrooms, and two flexible bonus spaces, the home can accommodate multigenerational living, private offices, fitness or hobby rooms, and guest quarters. Outdoor features include a covered lanai, pool, spa, and golf course views. The property is located near multiple highly rated golf courses, including TPC Prestancia, the Legacy Trail, parks, marinas, shopping, dining, and everyday conveniences, including Costco, Sprouts, Publix, and Target, with Whole Foods and additional retail coming soon. Siesta Key Beach, voted the number one beach in America, is located less than five miles away. Optional membership to TPC Prestancia Golf & Sports Club provides access to golf, tennis, pickleball, fitness facilities, a lap pool, dining, and social events. Club amenities are currently undergoing renovation and are expected to reopen soon, with discounted membership opportunities available before reopening. 3953 Prairie Dune Drive offers a large golf course home in an established gated community with flexibility and the opportunity to personalize in a location close to golf, the Legacy Trail, and Siesta Key.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-556-2150)
Listing Agent: Julianna Burns (941-800-7653)
530 MAGELLAN DR, SARASOTA, FL 34243
$625,00036 Days on yellowkey MLS ID: A4692098
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1720 Built: 1972 Tax: $6,126 (2025)Community: Whitfield Country Club Add RepSpa: YesSingle Family
Taxes:$6,126
Elementary School: Florine J. Abel Elementary
High School: Southeast High
Middle School: Electa Arcotte Lee Magnet
Remarks: Experience the pinnacle of Florida’s mid-century charm in this impeccably maintained 3-bedroom, 2-bathroom residence with a side entry garage, perfectly situated on a premier golf course lot. Lowest price on the 7th tee! This home has a private, resort-style oasis feel featuring a newly remodeled heated pool and spa, complete with modern Wi-Fi automation, outside security cameras & lighting, and a freshly re-screened cage—all framed by the lush, manicured fairways of the historic Sara Bay Country Club. Inside, the home shines with 2022 upgrades, including Luxury Vinyl Plank flooring and a comprehensive Trane HVAC system with new ductwork. Whether you are enjoying a morning coffee with panoramic golf course views or hosting an alfresco dinner under the mature palms, this property offers a rare move-in-ready lifestyle. For the golf enthusiast, an optional private membership to Sara Bay Country Club may provide access to the legendary Donald Ross-designed course and exclusive social amenities, allowing you to tailor your country club experience to your own pace. There is no mandatory HOA, but there are some special rules that apply to the neighborhood in the Manatee County Development Code that apply specifically to Whitfield. There is a voluntary Neighborhood Association for an annual fee of $30. The Sara Bay Country Club currently grants neighborhood association members a free culinary membership to the club, which grants limited dining privileges at the clubhouse. Schedule your showing today!
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Shaune Harper Kimbler (941-586-1394)
1350 SIESTA BAYSIDE DR #1350B, SARASOTA, FL 34242
$949,000118 Days on yellowkey MLS ID: A4683073
REDUCED by $26,000 (2.7%) on 05/27/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1495 Built: 1988 Tax: $8,303 (2025)Community: Gulf & Bay Club BaysideSpa: NoCondo
Taxes:$8,303
Remarks: Experience turnkey island living in this second-floor, three-bedroom townhome residence at Gulf & Bay Club Bayside on Siesta Key. Offered fully furnished and operating as an active rental with strong income history, this two-story getaway presents an outstanding opportunity for personal enjoyment and investment potential in one of Sarasota’s most desirable beach communities. Spanning nearly 1,500 square feet, the light-filled layout features tile flooring throughout the main living areas, high ceilings, and an open living/dining design ideal for gathering and entertaining. The updated granite kitchen is equipped with stainless-steel appliances, custom cabinetry, breakfast bar seating, built-in planning desk, and a sunny dining nook with additional storage. French doors open to the screened terrace, where added windows transform this space into a true year-round Florida room—an upgrade not commonly found in many Bayside residences. This enhancement expands the usable living area and allows you to enjoy the outdoor setting in every season, whether hosting guests or relaxing after a day at the beach. The primary suite is conveniently positioned on the main level and offers a walk-in closet, granite-appointed en-suite bath, and direct access to the enclosed terrace. Upstairs, a versatile loft provides flexible living space, while two guest bedrooms share a full bath—creating an ideal layout for visiting family or rental guests. This residence includes a deeded garage space and benefits from weekly rental flexibility, further enhancing its income-producing appeal. Unique Opportunity: We also have a second Gulf & Bay Club Bayside residence available in the same building on the first floor. Purchasing both properties would provide a rare chance to own five bedrooms within the same community—perfect for larger family gatherings, seasonal hosting, or multi-generational stays. Owners would enjoy the flexibility to occupy one unit while renting the other or maximize rental income throughout the year. Gulf & Bay Club Bayside is known for its coastal architecture and resort-style amenities. Residents enjoy heated swimming pool, tennis and pickleball courts, fitness center, clubhouse, grilling stations, and a fishing dock on the Intracoastal Waterway. Deeded beach access directly across the street places Siesta Beach’s renowned quartz sands and Gulf waters just moments away. Located in the heart of Siesta Key, this residence offers convenient access to Siesta Village’s restaurants, boutiques, and live music. Boating, paddle boarding, and waterfront dining are close by, while downtown Sarasota—home to the Sarasota Opera House, Selby Gardens, The Bay Park, and St. Armands Circle—is just a short drive away. Whether seeking a beach retreat, a rental investment, or the flexibility of dual-unit ownership on Siesta Key, this Gulf & Bay Club Bayside residence delivers location, versatility, and exceptional lifestyle value.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
7689 COVE TER, SARASOTA, FL 34231
$3,499,00050 Days on yellowkey MLS ID: A4691515
REDUCED by $196,000 (5.3%) on 05/27/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4564 Built: 1964Monthly Fee: $25 Tax: $18,202 (2025)Community: Southpointe ShoresSpa: YesSingle Family
Taxes:$18,202
Remarks: Just three homes in from the open waters of Little Sarasota Bay, this beautifully updated waterfront residence in Southpointe Shores offers a rare combination of location, scale, and immediate livability. Positioned on a quiet cul-de-sac with nearly 100 feet of Intracoastal frontage, the property captures wide water views and direct boating access in one of Sarasota’s most desirable neighborhoods. Spanning more than 4,500 square feet across two levels, the home is designed for both everyday comfort and entertaining. An open layout defines the main level, where wood-grain tile flooring connects the primary living spaces and walls of pocketing sliding glass doors open fully to the outdoor living areas—creating a seamless indoor-outdoor experience. The recently reimagined pool deck serves as the centerpiece of the home’s outdoor setting, featuring a covered lounge area, summer kitchen with built-in grill, and a resort-style heated pool and spa with sun shelf and waterfall features. The expansive patio overlooks peaceful waters, offering a dynamic waterfront backdrop from morning through sunset. Inside, the new chef’s kitchen has been thoughtfully updated (in 2024) with custom contemporary cabinetry, quartz countertops, high-end appliances—including a built-in Miele coffee station—center island with breakfast bar, and a full-sized wine cooler. The adjacent family room offers vaulted ceilings, water views, and a well-appointed wet bar with built-in shelving, creating a natural gathering space. Two guest suites with updated en-suite baths are located on the main level, along with a dedicated laundry room. The second floor is reserved for privacy, featuring an expansive primary suite with sweeping water views, fireplace, custom walk-in closet, and a marble en-suite bath. A study and additional bedroom on this level provide flexibility for a home office, fitness space, or nursery. Recent upgrades enhance both comfort and peace of mind, including impact windows and sliding glass doors (2020), a new seawall (2019), tile roof (2016), updated electrical wiring, modernized baths, and newer HVAC and water heater systems. Set on an oversized waterfront homesite with direct access to the Intracoastal Waterway, this boater’s sanctuary includes a newer private dock with 27,000-pound lift, accommodating a variety of boating needs. Southpointe Shores is a quiet, tucked-away waterfront community known for its proximity to Sarasota’s best coastal destinations. Siesta Key Beach and Crescent Beach are just minutes away, along with marinas, parks, and everyday conveniences. Downtown Sarasota’s cultural attractions—including The Bay Park, Selby Gardens, the Van Wezel Performing Arts Hall, galleries, and dining—are easily accessible, offering a lifestyle that balances privacy with connectivity.
1815 S LAKE SHORE DR, SARASOTA, FL 34231
$4,250,00062 Days on yellowkey MLS ID: A4690123
REDUCED by $250,000 (5.6%) on 05/19/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4177 Built: 2023 Tax: $32,460 (2025)Community: Oyster Bay EstatesSpa: YesSingle Family
Taxes:$32,460
Elementary School: Phillippi Shores Elementary
Remarks: Under contract-accepting backup offers. Experience refined modern living in this Oyster Bay Estates, stunning five-bedroom, four-and-a-half-bath residence thoughtfully designed and custom built with exceptional craftsmanship, elevated finishes, and sophisticated smart-home technology. Every detail of this home reflects a commitment to quality, comfort, and luxury. The heart of the home is an extraordinary chef's kitchen appointed with top-of-the-line Thermador appliances, custom cabinetry, an expansive island ideal for entertaining, and a striking custom hood. Elegant designer lighting and Emtek hardware compliment the home's extensive custom woodwork, including solid interior doors, crown molding, baseboards, and detailed window casings. Rich hardwood flooring flows throughout the living spaces, enhancing the home's warm yet refined aesthetic. Designed for both entertaining and everyday enjoyment, the home features a temperature-controlled 120-bottle wine cellar with WhisperKool system, a dedicated golf simulator room with Foresight simulator, and multiple thoughtfully designed living spaces. Smart-home technology is seamlessly integrated through a Wicked Smart system, controlling lighting, sound, security, shades, and WiFi, along with a Lutron automated lighting system throughout. The large and private outdoor living spaces are equally impressive, featuring a custom outdoor kitchen with integrated sound system, a resort-style pool and spa with sun shelf, and elegant travertine pool decking, creating the perfect setting for relaxing or entertaining under the Florida sun. Additional highlights include a striking custom solid oak entry door, designer-selected tile throughout, a built-in Elkay water dispenser, two laundry rooms for added convenience, landscape lighting and a spacious three-car garage. A rare opportunity to own a meticulously designed luxury residence where timeless craftsmanship, cutting-edge technology, and exceptional amenities come together in one remarkable Sarasota home.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Mary Pat Phillips Radford (941-587-9905)
3941 HAMILTON CLUB CIR #9, SARASOTA, FL 34242
$2,290,00096 Days on yellowkey MLS ID: A4685652
REDUCED by $100,000 (4.2%) on 04/02/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2856 Built: 1989Monthly Fee: $1,400 Tax: $15,416 (2025)Community: Hamilton ClubSingle Family
Taxes:$15,416
Remarks: Welcome to coastal luxury living in the exclusive Hamilton Club community on Siesta Key. This beautifully updated 3-bedroom, 3.5-bath WATERFRONT residence offers an exceptional blend of comfort, style, and boating convenience in one of the island’s most desirable locations. A spacious screened lanai overlooking the water creates the perfect setting for morning coffee, evening cocktails, and enjoying serene coastal breezes year-round. Designed for effortless everyday living and entertaining, the home features a private elevator, impact-rated windows and doors, and a private 10,000-lb boat lift with quick access to Sarasota’s waterways and the Gulf beyond. Each spacious bedroom includes its own en-suite bath, providing privacy and comfort for both residents and guests. Thoughtfully updated throughout, the residence showcases renovated bathrooms (2022–2023), kitchen enhancements completed in 2023, updated lighting throughout, and beautiful new wood flooring, all contributing to a refined coastal aesthetic. Additional upgrades include a new water softener and water pressure pump installed in 2025 for enhanced functionality and peace of mind. Offered furnished or unfurnished, the home provides flexibility for immediate enjoyment or personalization to suit your style. Hamilton Club residents will also benefit from upcoming community landscaping improvements this summer and exterior building painting scheduled for 2027, both covered by HOA dues. Ideally located just minutes from Siesta Key’s world-renowned beaches, dining, shopping, and entertainment, this exceptional waterfront residence delivers the ultimate combination of modern upgrades, private boating access, and relaxed island living.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Jennifer Thompson, Pa (941-928-0790)
6742 BOWLINE DR, SARASOTA, FL 34231
$450,00097 Days on yellowkey MLS ID: A4685028
REDUCED by $20,000 (4.3%) on 05/27/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1444 Built: 1969Monthly Fee: $3 Tax: $2,560 (2025)Community: Gulf GateSingle Family
Taxes:$2,560
Remarks: Motivated seller! Additional price reduction of $20K! One or more photo(s) has been virtually staged. If you're searching for an extra-large, fully fenced backyard in a quiet and private setting, this Gulf Gate gem may be exactly what you've been waiting for in a voluntary HOA community! This beautifully renovated home features a spacious split floor plan with two master suites, each offering large bathrooms—perfect for guests, multigenerational living, or added privacy. Major updates provide peace of mind, including a roof that is only 4 years old, A/C just 3 years old, and a water heater replaced 4 years ago. The home also features an updated kitchen with stainless steel appliances and stylishly updated bathroom vanities. The layout offers comfort, flexibility, and great functionality for everyday living. Enjoy the convenience of living just minutes from the world-famous Siesta Key Beach, along with easy access to Gulf Gate shops, restaurants, and nearby malls. Excellent A-rated schools make this location even more desirable. With its charm, valuable updates, and one of the most functional floor plans in Gulf Gate, this home offers comfort, convenience, and the best of a Florida lifestyle. Schedule your private showing today and contact your favorite Realtor before it's gone!
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Michelle Pino (714-588-0319)
4533 CINNAMON DR #2707, SARASOTA, FL 34238
$365,900111 Days on yellowkey MLS ID: A4683875
REDUCED by $14,000 (3.7%) on 05/27/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1638 Built: 2004 Tax: $2,681 (2025)Community: Arielle On Palmer Ranch Sec 1Spa: YesCondo
Taxes:$2,681
Remarks: Welcome to beautiful Palmer Ranch and the highly sought-after Arielle community! This spacious 2-bedroom, 2-bath condo offers the perfect blend of comfort, convenience, and resort-style living — all on one floor with no stairs. The bright, open-concept floor plan features tile flooring throughout the main living areas and carpeted bedrooms and den, abundant natural light, and a well-appointed kitchen with a brand-new dishwasher (2025). Recent upgrades include a brand-new A/C system installed in March 2025, providing peace of mind and energy efficiency. Both kitchen and dining room have tray ceilings. Step out onto your private screened lanai overlooking the community center and heated pool, offering a premium location just steps from the pool, spa, and grilling areas — perfect for relaxing mornings and peaceful evenings. Enjoy lush tropical landscaping, scenic walking trails, views of the pond, and resort-style amenities. Ideally located near the Legacy Trail, UTC, Costco, YMCA, Siesta Key beaches, shopping, dining, and I-75. No CDD and not in a flood zone. Schedule your private showing today!
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Jeffrey Reali (207-671-4091)
6703 MIDNIGHT PASS RD #208, SARASOTA, FL 34242
$299,999240 Days on yellowkey MLS ID: A4669017
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 702 Built: 1974 Tax: $3,626 (2024)Community: Sea WindsCondo
Taxes:$3,626
Remarks: LOWEST PRICE ON SIESTA KEY FOR A ONE BR CONDO OFFERING SHORT TERM RENTALS! Siesta Key Beach is calling you…experience the allure of coastal living at the quaint Sea Winds complex, conveniently located along Midnight Pass Rd., just a short walk to the world-renowned Siesta Key beach! This prime beach investment offering the opportunity to rent with a 2-week minimum and also use for yourself. This condo has an excellent rental history with bookings in place currently and into high season 2026. Average gross rental income is $20K/year with more upside potential. This delightful 2nd floor, generously sized 1 bedroom condo sustained NO damage from storms and comes fully furnished turn key offering desirable features such as a fully updated & equipped kitchen in on trend design, updated bathroom with new granite top vanity, tub/shower with new high end glass door, tile flooring, fresh bright paint colors, room for guests with convertible sofa, inviting dining space, open floor plan, AC 5 years new, H2O heater 2 years new, well maintained and move in ready! Easy parking with your own assigned space in front of your condo, plus guest parking. The Sea Winds is a small community of 35 units with amenities designed for year-round enjoyment, including bicycle rooms, a social room, shared laundry, pet friendly, and a heated pool complete with lounge chairs, umbrellas, and convenient bathroom facilities. Community pool had a complete upgrade in summer 2025. All buildings had new roofs in 2024 and experienced no major storm damage. The vibrant South Village is nearby, offering a variety of restaurants, boutiques, lively beach bars, ice cream shops, groceries, pharmacies and rental options for everything from fishing and boating to biking and kayaking. Plus, a daily trolley service stops right in front of the Sea Winds Condominium complex, providing easy access to all of Siesta Key's attractions. See this well priced condo today that is ready to go and a great investment on the Key!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Karen Nasello (727-421-0308)
3050 8TH ST, SARASOTA, FL 34237
$369,00072 Days on yellowkey MLS ID: A4688907
18 Days Off yellowkey (back on 5/27/2026)
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1636 Built: 1979 Tax: $3,004 (2024)Community: Avion OfSingle Family
Taxes:$3,004
Remarks: Diamond in the rough. This 3 bedroom and 3 bathroom home boasts over 1600sf and a pool. Perfect for a family or rental income. Each bedroom has its own en-suite bathroom. The kitchen and bathrooms have been updated. No HOA. The roof is 3 years old, pool surface recently refinished, pool pump replaced and tankless water heater. There is a large Florida room at the back of the home that leads out to a private pool and large yard that is completely fenced in for your privacy and perfect for entertaining. Beautiful sunsets as your barbecuing for all your guests on the large deck. Centrally located to all Sarasota attractions. Come put your finishing touches on this home and make it your own. Showings are by appointment only, please do not disturb the tenants.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Tom Machenheimer (941-321-5217)
2706 WHITE SANDS DR, SARASOTA, FL 34231
$414,50022 Days on yellowkey MLS ID: A4694861
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1600 Built: 1961Monthly Fee: $6 Tax: $3,654 (2025)Community: Gulf GateSingle Family
Taxes:$3,654
Remarks: Don't miss your chance to own a beautifully remodeled home in Gulf Gate, one of Sarasota's most sought-after locations. This 1600 Square Foot home on a quiet street is move in ready with nothing to do but sit back & enjoy. As you approach the home along the paver walkway & covered porch, you step through an impact rated door to a modern open-concept layout with elegant new luxury vinyl plank flooring. Large windows in the Living Room flood the room with light, and a wall of windows in the Dining Room brightens every meal. The large updated white kitchen has newer appliances, tile backsplash, and a breakfast bar. Oversized sliding glass door opens to a large backyard deck for entertaining and a paver patio perfect for a firepit and grilling. Mature trees and palms abound and set the tone for relaxing on a private lot with room for a pool. Split floorplan has two bedrooms and a tile bath with a tub down a short hallway from living areas at one end of the home. At the rear of the home, the primary bedroom has a vaulted ceiling with walk-in closet, en-suite updated tile shower, chair height toilet and sliding glass door that opens to the deck. Laundry and storage shelves in 1 car garage. Hot water heater replaced in 2026, Roof in 2025, and the Central Heat & Air (with insulated ductwork) and R-32 Attic Insulation in 2020. Professionally painted inside & out in 2026. Modern 6 panel doors with new hardware, 4 ceiling fans and wide window blinds on replacement double pane windows throughout. Lovingly owned and updated by long term owners. Great schools, shopping, and Gulf Gate Village restaurants within easy walking distance. Area beaches, churches, and vibrant arts and culture a short drive away.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Bob Moffatt (941-232-3370)
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