Location: Sarasota
Do Not Show Listings
6136 HOLLYWOOD BLVD, SARASOTA, FL 34231
$1,775,000175 Days on yellowkey MLS ID: A4674886
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2121 Built: 2016 Tax: $17,739 (2024)Community: 1206 - Aqualane Estates 3Rd UnitSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$17,739
Elementary School: Phillippi Shores Elementary
High School: Riverview High
Tax Year: 2024
Middle School: Brookside Middle
Remarks: Built in 2016, this exquisite home is perfectly positioned at the end of a highly coveted canal in Aqualane Estates, offering unparalleled privacy and breathtaking water views. Designed with both elegance and resilience in mind, the property remained completely unscathed during Hurricanes Helene and Milton (12.5 feet above sea level as well as impact windows/slider), providing peace of mind for future homeowners. This exceptional 3-bedroom, 2-bathroom residence boasts soaring 10-foot ceilings, luxurious marble finishes, and a versatile bonus room—ideal as an office, playroom, or creative space. At the heart of the home, the open-concept living area seamlessly blends indoor and outdoor living, making it perfect for entertaining or unwinding in style. Step outside to your private waterfront oasis, where a stunning pool and hot tub (added in 2021) set the stage for unforgettable sunsets over the canal. Boating enthusiasts will appreciate the convenience of direct backyard access to Sarasota Bay, allowing for effortless days on the water. Beyond the home’s serene waterfront setting, you’re just one mile from pristine powdery sand beaches and mere minutes from Siesta Key Village, as well as everyday essentials like Publix, Costco, and more. Whether you’re seeking a full-time residence or a luxurious retreat, this Aqualane Estates gem offers the best of Florida living. Home can be purchased Fully Furnished and ready to be moved into!
Listing is courtesy of: SOLUTIONS REALTY (941-302-4812)
Listing Agent: Priscilla Gratton (941-737-9100)
8092 GRANDE SHORES DR, SARASOTA, FL 34240
$1,499,99920 Days on yellowkey MLS ID: A4693313
1 Days Off yellowkey (back on 5/20/2026)
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2718 Built: 2019Monthly Fee: $433 Tax: $18,865 (2025)Community: Lakehouse Cove At Waterside Ph 1A & 1BSingle Family
Taxes:$18,865
Elementary School: Tatum Ridge Elementary
High School: Booker High
Tax Year: 2025
Middle School: McIntosh Middle
Remarks: Under contract-accepting backup offers. Experience luxury waterfront living in Lakehouse Cove at Waterside, one of Lakewood Ranch’s newest and most sought-after communities. Built by Homes by Towne, this custom Islander model offers 3 bedrooms, 3 full baths, a private study, formal dining room, oversized great room, and a spectacular outdoor living space with serene water views. From the moment you enter, expansive waterfront views set the tone for this thoughtfully designed open-concept home featuring extensive custom woodwork, shiplap accents, crown molding, and designer details throughout. The spacious great room showcases wood beam tray ceilings, custom built-ins, and 16-foot sliding glass doors that seamlessly blend indoor and outdoor living. The chef’s kitchen is designed for both entertaining and everyday living, featuring painted shaker cabinetry, quartz countertops, newer stainless steel built-in appliances with gas cooktop, custom subway tile backsplash, a large walk-in pantry, and an oversized island with seating. The luxurious owner’s suite offers peaceful water views, custom tray ceiling details, dual vanities, an oversized walk-in shower, ceramic tile flooring, and a custom-designed walk-in closet. Two additional guest bedrooms provide ample space and privacy, including one en-suite bath. A widened private study, spacious laundry room with built-ins and utility sink, drop zone, and attached three-car garage complete the interior. Step outside to the screened paver lanai overlooking unobstructed water views. The outdoor living area features a custom heated PebbleTec saltwater pool with sun shelf and tanning area, covered entertaining spaces, and a fully equipped outdoor kitchen with built-in, brand new gas grill and sink. New pool heater and pool lights were recently installed. Residents of Lakehouse Cove at Waterside enjoy resort-style amenities including a community center, fitness center, boathouse with kayak launch and storage, pickleball and bocce courts, dog park, and ferry access on Sundays to Waterside Place featuring shopping, dining, entertainment, and recreational activities.
Listing is courtesy of: SERHANT (646-480-7665)
Listing Agent: Jenn Flanders (941-232-0788)
3105 TRUSTEE AVE, SARASOTA, FL 34243
$400,000148 Days on yellowkey MLS ID: A4677124
REDUCED by $15,000 (3.6%) on 04/25/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1579 Built: 2018Monthly Fee: $317 Tax: $5,722 (2024)Community: University VillageHalf Duplex
Taxes:$5,722
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. This Charming, move-in ready home features 2 bedrooms plus a den, 2 bathrooms, and a 2-car garage, all complemented by stunning lake views. Nestled within a gated community, it is conveniently located just minutes from downtown and in close proximity to renowned beaches, shopping centers, schools, fine dining, golf courses, and the airport. The residence boasts an open great room concept, seamlessly connecting the living spaces with a fully equipped kitchen, making it ideal for entertaining family and friends. The covered and screened patio, pre-plumbed for gas and water, provides a private retreat with picturesque views of the lake and surrounding nature. Constructed to high standards, this home is equipped with hurricane shutters and has not sustained any damage from prior hurricanes. Additionally, it is situated outside of flood zones. The community offers a range of amenities, including a clubhouse with a heated pool and spa, a dedicated grilling area, and a dog park. The HOA fees encompass landscaping, exterior painting and pressure washing of homes, as well as internet and cable TV services. All Information to be verified by Buyers Agent
Listing is courtesy of: TRU LIFE REAL ESTATE LLC (614-584-0205)
Listing Agent: Khalil Rabah (614-584-0205)
1350 5TH ST #402, SARASOTA, FL 34236
$695,00016 Days on yellowkey MLS ID: A4691938
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 784 Built: 2019Monthly Fee: $724 Tax: $5,936 (2025)Community: Risdon On 5ThSpa: NoCondo
Taxes:$5,936
Elementary School: Alta Vista Elementary
Middle School: Booker Middle
Remarks: Stunning one bedroom penthouse in the heart of the Rosemary District, one of downtown Sarasota’s most vibrant and sought after neighborhoods, featuring an exclusive private garage, an exceptionally rare offering in luxury condo living. Positioned on a private penthouse level with only four residences, this sophisticated urban retreat combines privacy, security, contemporary design, and unmatched walkability. Filled with natural light, the residence features soaring ceilings, impact rated windows and doors, electric blinds, and refined modern finishes throughout. The open concept layout is complemented by a beautifully appointed kitchen with a premium appliance package, sleek cabinetry, and an oversized single cell sink designed for both style and functionality. Designed by Halflants + Pichette Studio for Modern Architecture, Risdon on 5th showcases striking contemporary architecture and an elevated downtown Sarasota lifestyle. Step outside your door to enjoy the rooftop pool and observation lounges, offering resort style amenities and an elevated atmosphere perfect for relaxing or entertaining. The gated community provides peace of mind while placing you in the center of downtown Sarasota’s thriving arts and entertainment scene. Residents enjoy unbeatable walkability to the Sarasota Opera House, theaters, acclaimed dining, rooftop bars, art galleries, boutique shopping, coffee shops, nightlife, and waterfront attractions. The private one car garage is a true rarity for downtown Sarasota penthouse living, adding convenience and long term value rarely found in the Rosemary District. Ideal as a full time residence, seasonal retreat, or investment opportunity, this exceptional penthouse offers the perfect lock and leave lifestyle in one of Sarasota’s most desirable urban locations.
Listing is courtesy of: THE KEYES COMPANY - SARASOTA (941-362-4100)
Listing Agent: Joseph Mcdonald, Llc (941-375-9646)
7287 ELEANOR CIR #15, SARASOTA, FL 34243
$339,00055 Days on yellowkey MLS ID: A4689525
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2228 Built: 1984Monthly Fee: $557 Tax: $1,957 (2025)Community: Pinehurst Sec IVilla
Taxes:$1,957
Elementary School: Kinnan Elementary
High School: Braden River High
Middle School: Braden River Middle
Remarks: You won't want to miss this open and spacious 2/2 Maintenance Free Villa with a huge den/office (possible third bedroom). Located in desirable Pinehurst Village Community within the Palm Aire Country Club Neighborhood. This home is nestled in this lovely quiet serene neighborhood. You will find this home features a large open Living - Dining room concept with vaulted ceilings, A full sized eat in kitchen with Quartz Countertops and GE appliances. A very spacious master bedroom features a private bath and over sized 6'x 10' walk-in closet. Plenty of room for family and friends in the second bedroom which also features its own walk in closet. Huge glassed in, tiled lanai off the living room, master bedroom and den. Easy to maintain ceramic tile and luxury vinyl thru out this magnificent home. Spacious two car garage with storage cabinets, workbench and overhead an overhead rack to finish off some great storage options. A rather long driveway for off street parking. You'll also find a full size washer and dryer laundry room off the kitchen area. Community pool, Clubhouse for special events you might want to host along with tennis courts. Close to Rt 75, Downtown Sarasota, Bradenton and the Beautiful Gulf Beaches, Golf Courses, UTC Mall, the upcoming Mote Aquarium, shopping and dining. Minutes to SRQ Airport, and a short drive to TPA, RSW, PGD airports are 60-90 mins away. This is the perfect location to enjoy the Florida life style. Enjoy the mixture of Villa's, Condo's, Single Family Homes that make living amongst the many preserves and lakes within a golf course community a pleasure to live. This is the perfect location to enjoy the Florida life style. Located adjacent to Palm Aire Country Club, membership is not required but multiple membership levels are available through the country club. BETTER HURRY AT THIS PRICE AND IN THIS NEIGHBORHOOD, THIS HOME WILL NOT LAST!!!!!!
Listing is courtesy of: MEDWAY REALTY (941-375-2456)
Listing Agent: Jonathan Woods (941-356-7583)
7280 ELEANOR CIR #101, SARASOTA, FL 34243
$231,00058 Days on yellowkey MLS ID: A4688357
REDUCED by $4,000 (1.7%) on 05/06/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1064 Built: 1993 Tax: $1,570 (2025)Community: Pinehurst Sec ISpa: NoCondo
Taxes:$1,570
High School: Bayshore High
Remarks: Welcome to Pinehurst at Palm Aire, This immaculate ground floor end unit that shows like a model! You'll enjoy the open light and bright feeling of this Split Plan bedrooms. Large windows and sliding glass doors make this a light, bright, airy space. Enjoy the privacy of the lush preserve behind the unit while sitting on your screened in lanai, accessible from both the living room and master bedroom. The UPDATED KITCHEN offers ample cabinets and counter space featuring newer granite counter tops and a breakfast bar that opens to the great room. The OPEN CONCEPT features tile flooring throughout the unit in the great room, dining room, kitchen, bedrooms, bathrooms and laundry room. UPDATED BATHROOMS with new countertops, In addition the unit features newer ceiling fans and A/C 2017, ROOF replacement 2016 by the condominium association. The Master suite features a large walk-in closet and private master bath with walk-in shower. A large second bedroom accommodates guests well with close proximity to the second full bath featuring a newer vanity with stone counter top and full sized tub. The separate laundry room includes washer/dryer, storage area, and water heater, has tile flooring and is brightened by a window. Your one car GARAGE houses your vehicle and plenty of storage. With only a short walking distance to the community pool, tennis and great walking areas. this Pinehurst condo is also ideally located with a short drive to SRQ International Airport, RSW,PGD, TPA airports an hour away. Some of the best shopping and restaurants are just minutes away. The UTC Mall. Convenient to all the area has, downtown Sarasota or Lakewood Ranch, the Gulf beaches 20-25 mins and easy access to the interstate. You can join nearby Palm Aire Country Club, a full-service country club featuring 36 hole year-round golf, dining, tennis, pickleball, water aerobics, and various social activities and events.
4005 CROCKERS LAKE BLVD #24, SARASOTA, FL 34238
$159,00021 Days on yellowkey MLS ID: A4693679
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 572 Built: 1989 Tax: $1,596 (2025)Community: Vintage GrandCondo
Taxes:$1,596
Elementary School: Gulf Gate Elementary
Middle School: Sarasota Middle
Remarks: Furnished, Move-In Ready Condo – Vintage Grand, Sarasota Your private oasis awaits! This beautifully appointed condo offers comfort, style, and convenience: Bedrooms/Bathrooms: Featuring Brazilian Cherry wood bedroom floors and ceramic diagonal tile in the living & kitchen areas. Kitchen & Bath: Upgraded wood cabinets, granite counters, and stainless steel appliances. Extras: New ceiling fans, washer/dryer, and 2 covered parking spots. Views: Enjoy serene lake and fishing pier views plus spectacular sunrises. Pet-Friendly: Small pets welcome! Community Amenities: Clubhouse, 2 pools, fitness center, and car washing area. Conveniently located near Olympic Swimming at Potter Park YMCA, COSTCO, shopping, dining, and dozens of golf courses. Easy access to Siesta Key Beach (just a few miles away) and local attractions like the famous Siesta Key Drum Circle. Whether you love staying active outdoors, lounging at the beach, or enjoying community amenities, this condo is perfectly located to make the most of Sarasota living.
Listing is courtesy of: PROJECT MANAGEMENT REALTY (941-979-6324)
Listing Agent: Dmytro Ivanov (941-979-6924)
344 W ROYAL FLAMINGO DR, SARASOTA, FL 34236
$6,850,00022 Days on yellowkey MLS ID: A4693231
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4344 Built: 1998Monthly Fee: $108 Tax: $51,269 (2025)Community: Bird KeySpa: YesSingle Family
Taxes:$51,269
Elementary School: Southside Elementary
Remarks: Open bay sunsets, deep water access, and timeless coastal architecture define this exceptional Bird Key waterfront residence. Positioned on a quiet cul-de-sac along Sarasota Bay, this extensively updated bayfront home offers panoramic open water views, refined living spaces, and direct Gulf access with no fixed bridges. With approximately 100 feet of waterfront frontage and a new dock completed in 2023 accommodating up to a 60-foot vessel, the property is ideally suited for both motor yachts and sailboats while embracing Sarasota’s boating lifestyle. Inside, the residence balances warmth and scale with expansive living spaces, detailed millwork, and a thoughtful floor plan designed for both everyday comfort and entertaining. Beautiful renovations throughout have created a move-in ready environment, including a completely remodeled primary bedroom and bath, a full kitchen renovation in 2023 featuring Sub-Zero and Viking appliances, updated second-floor bathrooms, redesigned TV room with custom fireplace and cabinetry, and a temperature-controlled 140-bottle wine wall and bar installation. Walls of hurricane-rated Pella windows and sliding doors frame open bay views while allowing natural light to move throughout the interiors. Marble, wood, and carpeted flooring, custom cabinetry, wood-paneled accents, and integrated audio systems contribute to the home’s tailored yet inviting atmosphere. Additional upgrades include a replaced seawall, resealed and painted roof, fresh exterior paint, replaced garage doors, sealed driveway, instantaneous hot water system, and updated air conditioning systems. Outdoor living is centered around sweeping sunset views, expansive waterfront terraces, and the privacy of a generously sized homesite within Bird Key. Residents enjoy immediate access to downtown Sarasota, St. Armands Circle, Lido Beach, Bird Key Yacht Club, and the area’s renowned dining, shopping, and cultural attractions while returning home to the quiet character of this residential island community. A beautifully maintained bayfront residence offering exceptional boating access, open water views, and a location that remains one of Sarasota’s most desirable waterfront settings. Private showings available by appointment.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Gigi Silverberg (941-993-3695)
4939 PEREGRINE POINT WAY, SARASOTA, FL 34231
$1,685,000127 Days on yellowkey MLS ID: A4680225
REDUCED by $114,000 (6.3%) on 04/07/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3828 Built: 2000Monthly Fee: $196 Tax: $8,043 (2025)Community: The LandingsSingle Family
Taxes:$8,043
Remarks: Under contract-accepting backup offers. A Masterpiece in The Landings' Most Coveted Enclave. Presenting a rare opportunity to acquire an impeccably crafted residence on the sought-after cul-de-sac of Peregrine Point Way. Built in 2002 with meticulous attention to feng shui principles, this single-level sanctuary spans over 3,800 square feet of thoughtfully designed living space, offering the perfect blend of sophistication, flow, and modern convenience. Grand First Impressions A circular driveway sets the stage for this distinguished residence. Pass through custom wooden gates into an impressive formal Florida entry courtyard, where a striking bronze fountain creates an unforgettable "wow factor" for arriving guests. This exceptional entry experience speaks to the caliber of craftsmanship found throughout. Exquisite Interior Details Marble flooring flows gracefully throughout the main living areas, establishing an elegant foundation for refined living. The thoughtful split floor plan ensures both privacy and space, while the single-level design provides effortless flow, a rare find in the homes of this caliber. The formal living room exemplifies true feng shui design, creating a seamless visual and physical connection to the resort-style outdoor spaces beyond. An adjacent formal dining room provides the perfect setting for sophisticated entertaining, whether hosting intimate dinners or grand celebrations. Luxurious Private Quarters The expansive primary suite serves as a serene retreat, featuring a spa-inspired marble bath with a soaking tub, dual vanities, and a walk-in shower. A generously proportioned custom walk-in closet provides exceptional organization and storage. Each of the home's four bedrooms includes an ensuite bathroom, a hallmark of luxury living that ensures privacy and comfort for family and guests alike. Custom-built closets throughout reflect the meticulous attention to detail. The fourth bedroom, currently appointed as an office with custom built-in cabinetry, offers flexibility for those who work from home or desire a private study. Resort-Style Outdoor Living. Step outside to discover your private oasis. The expansive screened-in lanai extends your living space into nature, perfect for year-round entertaining in comfort. The stunning pool area features a dramatic tall tile fountain whose soothing sounds create an atmosphere of tranquility. Mature landscaping artfully balances sun and shade, while a covered seating area invites quiet contemplation or spirited conversation. This is outdoor Florida living at its finest designed for those who appreciate the art of entertaining and the beauty of serene moments alike. The Landings Lifestyle. Peregrine Point Way's naturally serene cul-de-sac location is among the most desirable in The Landings. This prestigious community offers winding tree-canopied roads, pristine lakes, nature trails, and Roberts Bay access an idyllic backdrop for an elevated lifestyle.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Judy Greene (941-350-0451)
8311 FLAGSTAFF WAY, SARASOTA, FL 34241
$879,90042 Days on yellowkey MLS ID: A4689674
1 Days Off yellowkey (back on 5/2/2026)
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2892 Built: 2000Monthly Fee: $183 Tax: $5,513 (2025)Community: Preserve At Misty Creek Ph 02 TheSpa: YesSingle Family
Taxes:$5,513
Elementary School: Lakeview Elementary
Remarks: Under contract-accepting backup offers. Tucked away at the end of a quiet cul-de-sac, across from dedicated preserve land and within the gates of The Preserve at Misty Creek, 8311 Flagstaff Way offers a rare blend of relaxed Florida living and near proximity to all Sarasota has to offer. Set on nearly half an acre of beautifully landscaped, lakefront property, this residence feels like a retreat—where mornings begin with tranquil water views and evenings unfold under the soft glow of your own outdoor fire pit. Spanning nearly 2,900 square feet, this single-story home has been carefully improved and maintained over the years, creating a move-in-ready experience with both style and substance. Inside, volume ceilings, crown molding, and an abundance of natural light create a warm and open atmosphere. The kitchen and family room flow seamlessly together, anchored by a fully remodeled kitchen featuring solid wood cabinetry, stone counters, updated lighting, and stainless-steel appliances including a wine refrigerator. The home has seen extensive interior enhancements, including updated flooring, bedroom carpeting, interior painting, and refined finishes throughout. Both the kitchen and bathrooms have been tastefully remodeled, increasing the value of the home. Major systems and functional upgrades provide peace of mind. The property features NEW TILE ROOF 2024, two newer air conditioning systems, updated electronic heat assembly, and a variety of mechanical improvements that reflect careful ownership. Additional updates include refrigerator, garbage disposal, washing machine and dishwasher, along with improvements to lighting both within the home as well as outdoors. Hurricane resistant PGT windows ensure peace of mind. Step outside and the lifestyle truly comes to life. The screened, heated pool and spa overlook the lake, framed by updated and sealed pool pavers and a refreshed enclosure. A newer pool heater, motor, and actuator ensure everything operates seamlessly. The outdoor living space has been expanded with a custom patio and fire pit area for entertaining or simply unwinding. The grounds have been thoughtfully maintained and enhanced, including irrigation system updates and landscape improvements, to maximize both usability and aesthetics. Additional exterior improvements include garage upgrades with new door components and opener. Located in an X flood zone and built with solid block construction, the home combines durability with comfort. The side-entry garage includes a workshop space, adding functionality for hobbies or storage. Living in Misty Creek means enjoying a 24-hour guard-gated community with LOW HOA fees, SPACIOUS LOTS, and OPTIONAL golf membership. Sidewalk-lined streets for walking and cycling, a peaceful animal preserve setting, and access to fishing and bird watching create a lifestyle that is simultaneously active and serene. Luxury of top-rated schools, including The Classical Academy, are nearby. With just a short drive to the pearlized quartz sand of Siesta Key Beach, a multitude of dining options, and cultural amenities including theater, galleries, ballet, opera, circus and live music, this home offers the perfect balance of privacy and convenience. 8311 Flagstaff Way is more than just a home—it’s a property that has been continually improved, carefully cared for, and thoughtfully elevated to offer its next owner a truly effortless Florida lifestyle. Listing agent resides in this phenomenal community!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Lynne Zettergren (860-384-3132)
4881 ANTRIM DR, SARASOTA, FL 34240
$699,000139 Days on yellowkey MLS ID: A4678761
0 Days Off yellowkey (back on 5/20/2026)
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3588 Built: 2019Monthly Fee: $204 Tax: $7,803 (2025)Community: Worthington-Ph 1Single Family
Taxes:$7,803
Remarks: Under contract-accepting backup offers. HUGE PRICE IMPROVEMENT !! CAN NOT BEAT THIS PRICE NOW !! PRICED TO SELL NOW !! Absolutely Move In READY and Immaculately Maintained. A rare Opportunity to own a refined luxury residence in the coveted gated community of Worthington in Sarasota. This Exceptional Wekiva Floor Plan built by M/I Homes features 5 bed, 3 Full Bath, Bonus Room and 3 car Tandem garage with over 3500 Heated Sq Feet of thoughtfully designed living space, modern upgrades and flexible layout. From the Moment you arrive, the home's freshly done landscaping appeal sets tone, featuring paver driveway, tile roof. Step inside to a bright, open interior where natural light fills the space, highlighting tile flooring and refined architectural details. Home Features Brand NEW Refrigerator, Gourmet Kitchen, Stainless Steel Appliances, Built in Speakers, roller shades, plantation shutter, gas stove, quartz countertops. Step Outside to your private backyard oasis with expansive extended lanai with sliding glass doors. There is a plenty of space to make a POOL. NO CDD Fees, located near top schools, close to shopping, beaches, etc.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Fevil Patel (941-993-7286)
1514 S LAKE SHORE DR, SARASOTA, FL 34231
$1,895,00080 Days on yellowkey MLS ID: A4684167
2 Days Off yellowkey (back on 5/20/2026)
REDUCED by $80,000 (4.1%) on 04/28/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2430 Built: 1953 Tax: $14,799 (2025)Community: Oyster Bay EstatesSpa: YesSingle Family
Taxes:$14,799
Remarks: Located in the sought-after West of Trail neighborhood of Oyster Bay Estates, this beautifully updated residence sits on nearly one-third of an acre just around the corner from the historic Field Club. The home blends timeless architectural character with extensive recent improvements, creating a refined yet relaxed retreat close to Sarasota’s most desirable destinations. A beautifully landscaped yard and newly added covered front porch with brick pavers create inviting curb appeal and lead to a charming courtyard entry. Inside, the home showcases distinctive craftsmanship and warm architectural details, including Mexican tile floors, natural wood cabinetry and baseboards, exposed ceiling beams, plantation shutters, and hand-crafted clay sconces and pendant lighting. Fresh interior and exterior paint, updated trim, solid-core doors, and impact-rated windows and doors complement the home’s original character while adding modern comfort. The main living spaces flow naturally together, with the kitchen, dining area, and living room opening through walls of glass to the expansive screened lanai. A wood-burning fireplace with carved stone mantel anchors the living room, while a newly detailed tray ceiling adds architectural interest. The kitchen combines artisanal style with high-end functionality, offering custom wood cabinetry, updated countertops, an intricate ceiling detail, and premium appliances including a Sub-Zero refrigerator and Fisher & Paykel dual-fuel range with side-by-side ovens. Privately positioned, the primary suite features vaulted ceilings with exposed wood beams and sliding glass pocket doors that open directly to the pool terrace. Two walk-in closets with newly designed systems lead to the renovated primary bath, which offers dual vanities, private water closets, and a spacious walk-in shower. Two generously sized guest bedrooms provide comfortable accommodations, each with built-in closet systems and beautifully renovated en-suite baths, creating privacy for family and guests within the home’s traditional split floor plan. Outdoor living is designed for both relaxation and entertaining. The screened lanai surrounds a 40-by-14 heated pool framed by stone columns and generous covered seating areas with wood ceilings, while an Ipe wood open deck, fire pit, and lush tropical landscaping create a private backyard sanctuary. Additional improvements include updated plumbing and HVAC throughout, new ductwork and attic insulation, LED lighting, a Sonos sound system in the main living area and covered porch, renovated laundry room with new cabinetry and appliances, epoxy garage flooring, and a propane tankless water heater with gas supplied to the kitchen range and outdoor grill. Ideally located close to shopping, dining, and just minutes from world-renowned Siesta Beach and downtown Sarasota, this Oyster Bay Estates home offers a rare blend of character, privacy, and thoughtful updates in one of Sarasota’s most established neighborhoods.
Listing Agent: Michael Hays (941-376-1826)
4554 COOPER RD, SARASOTA, FL 34232
$1,250,000113 Days on yellowkey MLS ID: A4682274
REDUCED by $50,000 (3.8%) on 05/20/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3354 Built: 1958 Tax: $4,552 (2025)Community: Not ApplicableSingle Family
Taxes:$4,552
Remarks: Rare 3.2-acre private pool estate in Sarasota featuring a main residence and separate updated guest home—all set against tranquil pond views and lush, professionally designed landscaping. Accessed by a private road, this exceptional property offers complete privacy, multiple dwellings, and extraordinary flexibility for multigenerational living, rental income, recreation, or future development. Despite its peaceful, secluded setting, the estate is just minutes from Sarasota’s world-renowned beaches, vibrant downtown, premier shopping and dining, top-rated hospitals, parks, and the airport. Opportunities to own this level of acreage, privacy, and versatility in such a prime location are exceedingly rare. 2 car garage, carport and outbuilding included. Low taxes. No HOA. Sarasota County just outside city limits.
Listing is courtesy of: PRIME TIME REAL ESTATE INC (941-323-8685)
Listing Agent: Dan Novak (941-323-8685)
5175 CANTABRIA CRST, SARASOTA, FL 34238
$630,000217 Days on yellowkey MLS ID: A4669843
REDUCED by $44,000 (6.5%) on 04/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2377 Built: 2002Monthly Fee: $684 Tax: $5,027 (2024)Community: Silver OakSingle Family
Taxes:$5,027
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Remarks: Welcome to the highly desirable GATED COMMUNITY of SILVER OAK. An impeccable community featuring MAINTENANCE FREE LIVING developed by the QUALITY BUILDER- GIBRALTAR. Why settle for unknown quality? Gibraltar is considered one of the best in Southwest Florida when this community was developed. This home was a seasonal residence, like new interior. Enjoy beautiful lakefront views from the minute you enter the home. Notice the custom features including IMPACT WINDOWS, volume trayed ceilings, wood floors, and custom mill work. The current homeowner has lovingly updated every room in the house including the chef’s kitchen with beautiful granite counters, glass tile backsplash and stainless-steel appliances. The breakfast area features lake views where you can enjoy your morning coffee watching the heron fish for breakfast outside your door. The star of the show is the view of the lake through the large 27-foot screened lanai where you can enjoy your favorite beverage as the Florida sunset paints the clouds. A separate formal dining area has plenty of room for family or neighbors to have an elegant meal or simply play cards. A built-in wine bar can be used as butler’s pantry or center for entertaining. The primary bedroom provides more lake views, custom millwork, and an upgraded ensuite spa-like bath where a dip in the garden tub can wash your cares away. Two closets provide plenty of storage. The split bedroom has lots of space for guests. The 3rd bedroom/office has double doors to easily become additional living/entertainment area. The garage is air conditioned and has a spotless polyaspartic (epoxy) floor. Silver Oak is located in the highly popular Palmer Ranch. The Legacy Bike Trail is adjacent to the community and allows you to ride, walk or jog to downtown Sarasota or Caspersen Beach in Venice. Plans are to ultimately link this to trails along the entire west coast of Florida. The home is few minutes from Costco, Target, Lowes and a plethora of other shopping.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Mark Midyett (941-556-5151)
2228 N ORANGE AVE, SARASOTA, FL 34234
$185,00020 Days on yellowkey MLS ID: O6408224
Bed: 4 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 1340 Built: 1925 Tax: $2,082 (2025)Community: NewtownSpa: NoSingle Family
Taxes:$2,082
Remarks: Meet 2228 N Orange Ave, a residence arranged for everyday practicality and comfortable living. The kitchen features all stainless steel appliances, complementing a primary bedroom that includes a spacious walk in closet for convenient organization. The property's exterior is enhanced by a fenced in backyard, featuring a storage shed, establishing a secure outdoor area. This home provides essential design and daily ease for you. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
4131 PRUDENCE DR, SARASOTA, FL 34235
$289,90020 Days on yellowkey MLS ID: A4693475
0 Days Off yellowkey (back on 5/18/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1145 Built: 1966 Tax: $1,675 (2025)Community: Kensington ParkSingle Family
Taxes:$1,675
Elementary School: Gocio Elementary
Remarks: ***More pictures on Monday. This 2 bedroom /2 bath single family home with one-car garage, shed and lanai, is located in Kensington Park and is a rare find! Kitchen has Formica counter tops with raised white cabinets and double bowl sink with stone back splash. Hall bath has tub/shower newer vanity and tile floors, luxury Vinyl Plank flooring throughout home. Hurricane impact windows and lanai. Kensington Park in the heart of Sarasota minutes from University Town Center Mall, Sarasota International Airport, downtown Sarasota, Gulf beaches and close to I-75.
Listing is courtesy of: REALTY SERVICES INC (941-954-4443)
Listing Agent: Kenneth Cowles (941-954-4443)
2932 LEXINGTON ST, SARASOTA, FL 34231
$1,000,00055 Days on yellowkey MLS ID: O6398095
REDUCED by $50,000 (4.8%) on 05/20/2026
Bed: 0 Bath: 0.0 Gar: 2 Liv Area Sq Ft: 4005 Built: 1978 Tax: $9,282 (2025)Community: Colonial TerraceApartment
Taxes:$9,282
Remarks: Welcome to this stunning income producing home located minutes to Sarasota's most desirable attractions such as Siesta Key Beach, Selby Gardens, Downtown Sarasota, Longboat Key, and University Town Center Mall. This home consists of 3 income producing units or make it your very own primary residence or vacation dream home. With 3 separate entry ways you can rent two and occupy one or join all 3 together to make it a luxurious family home. Can be sold as a package deal with #06399746,#06399737, #06399693, #06399686
Listing is courtesy of: FRAKES REALTY (508-717-2752)
Listing Agent: Derek Frakes (508-717-2752)
$1,000,00055 Days on yellowkey MLS ID: O6398108
Bed: 7 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4005 Built: 1978 Tax: $9,041 (2025)Community: Colonial TerraceSpa: YesSingle Family
Taxes:$9,041
1200 SIESTA BAYSIDE DR #1200G, SARASOTA, FL 34242
$425,00079 Days on yellowkey MLS ID: A4685175
REDUCED by $25,000 (5.6%) on 05/20/2026
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 845 Built: 1988 Tax: $4,441 (2025)Community: Gulf & Bay Club BaysideCondo
Taxes:$4,441
High School: Sarasota High
Remarks: Welcome to the world-famous Siesta Key! Now available a second-floor one-bedroom, one-bath condominium in the desirable Gulf and Bay Club Bayside. This particular condo had zero flood or storm damage. This home is just waiting for your personal touch! Enjoy direct deeded beach access just across the street to Siesta Key Beach and live a true resort-style life with wonderful amenities at your fingertips. An open floor plan greets you with tile on the diagonal, a spacious living/dining area, and a balcony overlooking the community pool. The unit is complete with a private one-car garage, indoor laundry with a brand-new stackable washer and dryer, and turnkey furnished and ready for you or your guests. Gulf and Bay Club Bayside features: Two resort-style pools Tennis and pickleball courts Newly renovated fishing dock Walking paths, boat loading zones, and four BBQ areas Clubhouse for private parties and events. This weekly-rental-friendly community also offers onsite management (directly below the unit), making it a great income opportunity for investors or those seeking a snowbird property. Location cannot be beat you just cross the road for beach access or take the free trolley to explore Siesta Key Village or South Siesta! Live the island lifestyle at Gulf and Bay Club Bayside. Tenant occupied best showing time Saturday but with enough notice we can manage a showing. Must be scheduled and approved by tenants.
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: Jessica Ross, Pa (941-321-9000)
5141 OAKLAND HILLS AVE, SARASOTA, FL 34234
$168,000370 Days on yellowkey MLS ID: O6310883
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 612 Built: 1960 Tax: $2,616 (2024)Community: Tri-Par EstatesMobile Home
Taxes:$2,616
Remarks: SELLER FINANCING AVAILABLE / LEASE OPTIONS AVAILABLE $2000 MO / Feast your eyes on this treasure! A completely remodeled 1-bedroom, 1-bathroom mobile home nestled in a lively 55+ community. Even better you own the land, not lot rent here. This beauty's had a head-to-toe makeover with all the modern flair you’ve been dreaming of. Picture yourself soaking up the breeze on a spacious screened-in patio. Whether it’s your cozy nest or your beach escape, this place is calling your name. Forget about monthly HOA fees because they’re wrapped up in your property tax. This community comes stocked with lots of great amenities from a community pool, bot tub, shuffleboard, and pickleball courts. Make sure to check out the clubhouse that offers a calendar of activities. Cable and trash service included. Location is everything! You’re just a hop, skip, and a jump from the Sarasota/Bradenton International Airport, with shopping, dining, hospitals, parks, and speedy access to I-75 right at your fingertips. Plus, you’re nearby the stunning beaches, and the lively downtown Sarasota and St. Armands Circle. Experience the peace and community vibes here—it’s a spot you’ll love to call home!
Listing is courtesy of: RE/MAX ASSURED (800-393-8600)
Listing Agent: Jason Buelow (407-450-6193)
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