Location: Sarasota
Keyword(s): Sarasota High
Keyword(s) High School: Sarasota High
Do Not Show Listings
4076 SOUTHWELL WAY, SARASOTA, FL 34241
$669,000122 Days on yellowkey MLS ID: A4682589
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2263 Built: 1979Monthly Fee: $27 Tax: $3,668 (2025)Community: Bent Tree VillageSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,668
Elementary School: Lakeview Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Sarasota Middle
Remarks: This is a rare opportunity to purchase a well built original Bent Tree home with newer roof right on the fairway of Bent Tree golf course. This beautifully maintained split plan residence offers privacy, thoughtful upgrades, and premium positioning within the neighborhood. Bent Tree Community Homeowners Association dues are only $319 per year. Situated on a premium lot on hole #16, it boasts a west-facing rear exposure to enjoy sunsets throughout the seasons and beautiful afternoon light situated on an elevated lot that you can see clearly from the roadway. The property has never experienced flooding and features many different exotic trees, including an original Bent Tree bottle brush,a maple tree in front, sycamore, camphor, and bamboo. The exterior showcases an authentic clay brick driveway, brick paver front entry, and decorative porcelain tile accents with evening lighting. Twelve-volt LED driveway lighting and professional 120-volt LED landscape lighting enhance the property’s curb appeal. Inside, the home features porcelain tile flooring throughout—no carpet. Recent improvements include new bathroom mirrors and Kohler faucets, 72-inch energy-efficient DC indoor/outdoor ceiling fans (6 total), and replaced sliding glass doors (11/2021). Most windows were replaced in 05/2021 with Armortech windows all under Sarasota County permit. Additional metal security panels provide extra hurricane protection for select windows. The property includes a well-fed, three-zone sprinkler system for lawn irrigation and a hot water heater timer for additional efficiency. Outdoor living is enhanced by two private bathroom courtyards finished with real brick pavers and Hardy Board fencing. The pool area is supported by updated equipment and energy-efficient systems. This property combines extensive upgrades, quality materials, and a prime golf course setting—ready for its next owner to enjoy.
Listing is courtesy of: GOOD LIFE REALTY LLC (941-342-9889)
Listing Agent: Raffilena Hamilton (941-685-2441)
6325 RIVO LAKES BLVD, SARASOTA, FL 34241
$850,0004 Days on yellowkey MLS ID: A4696525
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2418 Built: 2019Monthly Fee: $197 Tax: $8,716 (2025)Community: Rivo LakesSpa: YesSingle Family
Taxes:$8,716
Middle School: Riverview Middle
Remarks: Welcome to this stunning luxury pool home in Rivo Lakes, where style, comfort, and location come together seamlessly. This beautifully designed 4-bedroom, 3-bath residence with a spacious 3-car garage offers the perfect blend of elegance and everyday functionality. Step inside to discover an open and inviting floor plan enhanced by gorgeous wood-look tile flooring throughout, creating a cohesive and modern feel. The heart of the home flows effortlessly into your private outdoor oasis featuring a sparkling pool and spa, ideal for relaxing or entertaining year-round. Enjoy ultimate privacy in your backyard retreat, with no homes or roads behind you, creating a peaceful and secluded setting that’s hard to find. The primary suite is a true retreat, complete with two semi-custom walk-in closets which offer exceptional storage and organization. Each additional bedroom is generously sized, providing comfort and flexibility for family, guests, or a home office. Built for peace of mind, this home is equipped with hurricane impact windows, offering safety and energy efficiency. Perfectly located just 15–20 minutes from world-famous Siesta Key Beach and the vibrant UTC Mall and shopping district. You’ll enjoy convenient access to top-rated dining, shopping, and entertainment while savoring the tranquility of East Sarasota living. This is Florida luxury living at its finest. Schedule your private showing today.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Tracy Anderson (214-621-6128)
6415 MIDNIGHT PASS RD #211, SARASOTA, FL 34242
$799,900179 Days on yellowkey MLS ID: A4675481
REDUCED by $50,000 (5.9%) on 06/13/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2358 Built: 1975 Tax: $7,544 (2025)Community: AnchorageSpa: NoCondo
Taxes:$7,544
Elementary School: Phillippi Shores Elementary
Middle School: Brookside Middle
Remarks: Huge opportunity to own a spacious 2,400 sq ft, 3 bedroom condo on Siesta Key with an aggressive, new price drop! Now being offered at $799,900 - an unbelievable $339.22 per square foot (vs recent SK sales average of $460 per square foot). This is a fabulous family investment with plenty of room to sleep 8 people (Note: a 4th bedroom could easily be added). This condo has brand new floor-to-ceiling high impact hurricane sliders that run the entire length of the condo and open to a full 95’ lanai for a nice open-air feeling. Allow your family to enjoy your new vacation home, then use the successful in-house rental program to make additional income for yourself. The best of both worlds! Gated-community amenities abound here: both private beach access and intracoastal access with use of free boat slips and kayak racks. One of the largest heated pools on the Key. Brand new pickleball and tennis courts. Tropical landscaping that includes areas for nice seating on the intracoastal, outdoor grilling and picnics, shuffleboard, cornhole, and basketball goal. Fitness center and party/event space. Wheel-chair accessible property. You can go from car to kitchen with no steps! This condo offers a very desirable split floorplan with the primary bedroom on one end and the other two bedrooms on the opposite end with 2 distinct heating/cooling systems. Also includes 2.5 baths with both a tub and shower option. Generous closets in each room, plus a large owner’s closet, beach closet and unique private, full storage closet in hallway next to condo. Whether you are searching for a spacious family getaway, a peaceful primary residence, and/or a high-performing rental, this rare offering delivers.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Mina Johnson (941-404-9347)
5125 WILLOW LEAF DR, SARASOTA, FL 34241
$1,190,000104 Days on yellowkey MLS ID: A4683770
1 Days Off yellowkey (back on 5/30/2026)
REDUCED by $50,000 (4.0%) on 04/21/2026
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3837 Built: 1986Monthly Fee: $60 Tax: $8,339 (2025)Community: Bent Tree VillageSpa: YesSingle Family
Taxes:$8,339
Remarks: Under contract-accepting backup offers. An exceptional custom home by Arthur Rutenberg, set on nearly one acre behind the gates of Bent Tree Village, offers space, privacy, and thoughtful design in one of Sarasota’s most desirable communities. Step through the double wood doors into a welcoming foyer that opens to formal living and dining rooms, creating an immediate sense of openness. The layout flows naturally, making it just as comfortable for quiet evenings as it is for hosting guests. The kitchen is designed for someone who truly enjoys cooking. You’ll find generous counter space, extensive wood cabinetry with abundant storage, a breakfast bar, and a full suite of updated appliances, including a wine refrigerator. An informal dining area sits just off the kitchen, overlooking the screened lanai, pool, and spa, perfect for everyday meals with a view. The family room is spacious and inviting, anchored by an oversized wood-burning fireplace and complemented by a wet bar, an ideal setup for gatherings or relaxed weekends at home. The primary suite provides a private retreat with an ensuite bath featuring dual sinks, a water closet, a freestanding tub, and a step-in shower. Four additional bedrooms allow for flexibility. The fifth bedroom, with its own private entrance, can easily serve as a home office, game room, or guest suite. Outside, the screened pool and spa area is the true centerpiece. With nearly an acre of surrounding grounds, there’s ample room for entertaining, recreation, or simply enjoying the privacy and greenery. Located in a private gated community with convenient access to shopping, dining, golf, and the cultural amenities Sarasota is known for, this home offers the best of both comfort and location. And in walking distance to Lakeview Elementary School. Less then 5 miles to two private schools, the Classical Academy or Out of Door Academy. It’s a property that must be experienced in person to fully appreciate.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Lisa Bouck, Pa (941-374-0165)
3612 S LOCKWOOD RIDGE RD, SARASOTA, FL 34239
$689,0003 Days on yellowkey MLS ID: A4696876
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2895 Built: 1962Monthly Fee: $17 Tax: $3,014 (2025)Community: South GateSpa: NoSingle Family
Taxes:$3,014
Elementary School: Wilkinson Elementary
Remarks: Beautiful 4BR/3Bath Pool Home in the highly desirable Southgate neighborhood close to everything great that Sarasota has to offer. Sitting on a perfect rectangular 10,500 Sq’ lot the home boast 2895 Sq’ of indoor livingspace, offering plenty of room for multi-generational living or converting the primary suite (with 2 doors to the exterior) into a Mother-In-Law apartment or ADU (AuxiliaryDwelling Unit) as a possible income generator. When you enter the home, you are greeted by a massive living room and tastefully updated ceramic tile on the diagonal that carries throughout the home. The open plan main living areas are complemented with spacious split bedrooms for privacy. The light and bright kitchen has 2 windows and recessed LED lighting and ample stone counters that a cook or baker will appreciate, plus upscale Samsung black stainless steel appliances, and a breakfast bar to the bonus room that has 2 large pantry closets and a built in desk with shelves. French doors lead out to the paver brick; lanai, patio and sunny pool area, on a spacious fully fenced backyard. The home is on county water and sewer and has 9.5 year old roof, 2 zones of HVAC; one is 2021 14 SEER Trane 2 ton for the primary BR side of the home, and the other is a 13 year old 15 SEER 3.5 ton Comfortmaker that is serviced regularly for the rest of the home. Large overhanging roof provides shade for passive cooling and coverage for outdoor storage. Book your private showing and scoopup this great opportunity NOW!
Listing is courtesy of: ALBERT WOOSTER & COMPANY (941-350-1220)
Listing Agent: Albert Wooster (941-350-1220)
2915 WEBBER ST, SARASOTA, FL 34239
$399,9003 Days on yellowkey MLS ID: A4696773
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1290 Built: 1958 Tax: $2,275 (2025)Community: South GateSingle Family
Taxes:$2,275
Elementary School: Southside Elementary
Remarks: This beautiful property has granite countertops, shaker cabinets, a newer kitchen and bedroom has been totally remodeled about 6 years ago. It has brand new flooring. The air conditioning is about 7 years ago. There is nice rare brick pavers and patio with a large fenced in yard.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Curtis Putrino (941-302-8776)
2344 TEMPLE ST, SARASOTA, FL 34237
$575,0003 Days on yellowkey MLS ID: A4696470
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1000 Built: 1954 Tax: $3,291 (2025)Community: Loma Linda ParkSingle Family
Taxes:$3,291
Elementary School: Alta Vista Elementary
Remarks: Beautifully maintained 3-bedroom, 2-bath Sarasota home in a highly desirable location just minutes from downtown Sarasota, Sarasota Memorial Hospital, Southside Village, Midtown Plaza, Arlington Park, and the Legacy Trail. In addition to the square footage reflected in the public tax record, the home also offers an enclosed Florida room, creating a more spacious and flexible layout. Inside, you’ll find a cozy living room fireplace, a recently updated bathroom, and a versatile casita-style/mother-in-law-style suite ideal for guests, extended stays, a private office, studio, or additional everyday use. The roof was replaced in 2024, offering added peace of mind. Step outside to a beautifully landscaped backyard designed for relaxing and entertaining. The covered patio features recessed lighting, creating a warm and inviting outdoor living area, while the side yard includes a storage shed for added convenience. Location is a major highlight — approximately 5.5 miles to Lido Key Beach and approximately 6 miles to Siesta Key Beach, placing you close to two of Sarasota’s most beloved coastal destinations. Arlington Park & Aquatic Center is also nearby, offering pickleball and tennis courts, basketball courts, playgrounds, walking paths, dog-friendly areas, swimming pools, and community events. An exceptional opportunity to enjoy the Sarasota lifestyle with flexible indoor space, beautiful outdoor areas, and easy access to beaches, downtown, shopping, dining, and recreation.
Listing is courtesy of: EXP REALTY, LLC (941-462-3321)
Listing Agent: Jennifer Kenna (941-253-3003)
1900 BENJAMIN FRANKLIN DR #V11, SARASOTA, FL 34236
$799,0007 Days on yellowkey MLS ID: A4696174
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1242 Built: 1967 Tax: $5,712 (2025)Community: Lido HarbourVilla
Taxes:$5,712
Middle School: Booker Middle
Remarks: Beachside living awaits in this beautifully renovated, turnkey-furnished villa just steps from the sugar-white sands of Lido Beach. This two-bedroom, two-bath residence offers a relaxed island lifestyle in an unbeatable location. The thoughtfully redesigned interior features an open floor plan centered around a spacious great room. The kitchen is beautifully appointed with contemporary cabinetry, quartz countertops, stylish backsplash, and premium KitchenAid appliances, including an induction cooktop and beverage refrigerator. Stylish finishes throughout include large-format porcelain tile flooring, crown molding, recessed LED lighting with dimmer switches, and custom remote-controlled window treatments. The primary suite features a walk-in closet and ensuite bath, while both bathrooms offer floor-to-ceiling porcelain tiled walk-in showers with frameless glass enclosures, built-in niches, and LED lighted mirrors. Additional upgrades include updated plumbing and water lines, underground sewer drains, an updated electrical panel and wiring, and a newer A/C system. A large laundry room with built-in cabinetry, counterspace, Maytag washer and dryer, and direct access to the attached carport adds convenience and functionality. Located on the quiet southern end of Lido Key, this ground-level villa offers the privacy of a single-family home with the ease of maintenance-free living. Enjoy direct beach access and a heated Gulf-front pool with clubhouse just moments from your door. Ideally located near South Lido Park, St. Armands Circle, and downtown Sarasota, you'll enjoy easy access to dining, shopping, nature trails, kayaking, cultural attractions, and breathtaking Gulf sunsets. Move right in and start enjoying the best of Sarasota's beach lifestyle.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Judy Nimz (941-374-0196)
SARASOTA, FL 34242
$2,895,0003 Days on yellowkey MLS ID: A4694972
Bed: 5 Bath: 0.0 Gar: 2 Liv Area Sq Ft: 2966 Built: 2021 Tax: $24,633 (2025)Community: Point Of Rocks TerraceSpa: YesApartment
Taxes:$24,633
Remarks: There Is Only One. Crescent Beach House was purpose-built for a different kind of ownership experience. One where beach days, family gatherings, and investment performance can coexist under the same roof. Positioned in one of Siesta Key's most enduring vacation corridors, this is the type of property people return to year after year, and increasingly, seek to own. Sited at the mouth of the Point of Rocks’ beach access located at the end of the street, Crescent Beach House is a professionally designed luxury residence and high-performing short-term vacation rental offering five bedrooms, seven baths, an elevator, resort-style pool and spa, and expansive indoor-outdoor living spaces designed to accommodate large groups with ease. Unlike traditional vacation homes, the property was intentionally engineered for the demands of luxury short-term rentals, blending resort-style living with commercial-grade durability and operational efficiency. Whether enjoyed as a private family retreat, an income-producing asset, or a combination of both, the property offers a rare blend of lifestyle and investment performance. Only one adjoining residence is attached, creating a boutique ownership environment, while the neighboring property is also available for purchase separately for those seeking a larger footprint, future family compound opportunity, or multi-generational ownership strategy. Financial performance, rental history, ADR and RevPAR data available upon request.
Listing Agent: Rudy Dudon (941-234-3991)
7732 DONALD ROSS RD W, SARASOTA, FL 34240
$2,100,00044 Days on yellowkey MLS ID: A4692026
REDUCED by $150,000 (6.7%) on 06/12/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3686 Built: 1993Monthly Fee: $369 Tax: $15,084 (2025)Community: Laurel Oak Estates Sec 05Spa: NoSingle Family
Taxes:$15,084
Elementary School: Tatum Ridge Elementary
Middle School: McIntosh Middle
Remarks: Don’t miss this unique opportunity to own an "outstanding" 4-bedroom, 3.5-bath residence located within the gates of Laurel Oak. This home is ideally positioned on a ½ acre plus premium lake lot with exceptional "natural" privacy, serene water and preserve views from your picture framed lanai. Every home has a story, and this one began in 2020 when it was taken down to the studs and thoughtfully reimagined through a custom renovation—blending timeless design with modern functionality, and delivering a move-in ready experience with lasting peace of mind. The architectural details include crown molding, tray and volume ceilings that highlight the sense of openness and elegance throughout the living spaces. The kitchen has been meticulously designed with expansive counter space and custom cabinetry, creating a natural balance between everyday comfort and functionality. It’s a space that supports daily living with ease while also accommodating those moments that call for gathering and celebration, it is open, practical, and tailored to the flow of everyday life. The transition from the interior living spaces to the exterior spaces creates a true indoor-outdoor lifestyle: inviting, open, and designed for everyday living. Multiple access points from room to room including the Primary & Secondary en-suites extend the living space outward, connecting naturally to the expansive under-cover lanai and pool area showcasing postcard-worthy views with peaceful sightlines. It’s a layout that offers flexibility. Schedule your private showing today to experience this rare Laurel Oak Estates property. Residents have the option to join Laurel Oak Country Club, offering two 18-hole championship golf courses, 12 Har-Tru tennis courts, six pickleball courts, and an active social calendar. Ownership includes moving to the top of the waitlist and (next spot) priority placement on the country club waiting list. Beyond the gates, the location places you near shopping, dining, entertainment, medical facilities, major roadways, and Sarasota’s renowned beaches.
Listing is courtesy of: THE REAL ESTATE STORE (941-685-4224)
Listing Agent: William Kelly (941-685-4224)
3174 PEACHTREE ST, SARASOTA, FL 34231
$468,00038 Days on yellowkey MLS ID: A4692949
0 Days Off yellowkey (back on 6/12/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1548 Built: 1988 Tax: $4,143 (2025)Community: Flora-Villa SubSingle Family
Taxes:$4,143
Remarks: Under contract-accepting backup offers. An actual peach! This lovely sunshine-y home on Peachtree Street is ready for new memories to be made. Located right in the heart of Sarasota, the neighborhood of South Gate Ridge is 10 minutes from everything. This lofty, light filled house is one block from the locally adored Bee Ridge Park, where neighbors gather to play in local softball games; enjoy an evening walk with the puppy; push their kiddos on the swing; or tend to their vegetables in the robust community garden. Tucked back on this spacious lot, this home feels private and peaceful. Once inside, the open and airy floor plan is punctuated by an open loft that is framed by a beautiful wood bannister, adding warmth and dimension to the entire space. A LARGE Primary Suite with West facing windows, wide closets, and a newly remodeled double vanity bathroom, sits on the main level. The already sizable living room, anchored around a stone fireplace, feels even more voluminous with vaulted ceilings and large windows. A BRAND NEW kitchen has been recently completed featuring soft close cabinets and drawers with built in organizers. Coastal blue tiles add a vibrant pop of color that will be on trend for years to come. Upstairs, two large bedrooms share the cozy loft space as well as the freshly RENOVATED second bathroom. Large, New Impact Sliders open up the entire back of the home to the large private backyard with an awesome deck and room for a pool. A true two car garage has its own loft space for extra storage and the brand new washer and dryer conveys with the sale. NEW ROOF in 2023!! Fresh paint inside AND out. All this home needs is you ;) This peach of a property could not be cuter and is completely move-in ready!
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Kelly Drost (941-822-6926)
3231 BENEVA RD #103, SARASOTA, FL 34232
$175,000143 Days on yellowkey MLS ID: A4678445
REDUCED by $14,900 (7.8%) on 04/20/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 964 Built: 1978 Tax: $2,164 (2025)Community: Village Brooke Sec 3Condo
Taxes:$2,164
Remarks: Under contract-accepting backup offers. Welcome Home to this beautifully updated 2-bedroom, 2-bath first floor condo located in the highly desirable Village Brooke community. This move-in-ready residence has been thoughtfully renovated with brand new bathrooms, a stunning updated kitchen, and new appliances, offering a fresh, modern feel throughout. Enjoy the convenience of ground-floor living and unwind on your private screened-in back patio, perfect for relaxing or entertainment. Village Brooke is a well maintained, pride-of-ownership community featuring two community pools, tennis courts, and shuffleboard, all set among lush, beautifully cared-for grounds. Ideally situated, this condo offers central Sarasota living with easy access to shopping, dining, and everyday conveniences. I-75 is just minutes away, making commuting a breeze, and you’re perfectly positioned between Downtown Sarasota and UTC Mall, giving you the best of both worlds. Whether you’re looking for a primary residence or a seasonal retreat, this beautifully updated condo checks all the boxes! Don’t miss your chance to own a slice of comfort and convenience in Village Brooke!
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Andrea Capek (941-497-6060)
101 WHISPERING SANDS DR #107, SARASOTA, FL 34242
$475,000194 Days on yellowkey MLS ID: A4674069
REDUCED by $20,000 (4.0%) on 05/04/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1271 Built: 1969 Tax: $5,864 (2024)Community: Whispering SandsCondo
Taxes:$5,864
Tax Year: 2024
Remarks: One or more photo(s) has been virtually staged. Welcome to affordable GULF FRONT living! This is one of the best values in Whispering Sands. The seller is willing to offer a $60,000 SELLER CREDIT with an acceptable offer to offset any future improvements or assessments. This recently updated, 2 bed/2 bath, DOUBLE LANAI CORNER unit is nestled in the southwest corner of the popular Tropic View building, the Whispering Sands midrise closest to the Gulf and 800' of your own private beach! The freshly painted interior features NEW luxury vinyl plank flooring, NEW interior doors, and NEW overhead designer lighting and fans. Four sets of floor-to-ceiling sliders open from the living areas and bedrooms into TWO separate 24’ glassed and screened lanais – complete with epoxy flooring and NEW ceiling fans to capture the coastal breezes. After a full day at the beach, meal prep is easy in your partially open kitchen featuring NEW granite countertops, farmhouse style stainless sink, and NEW 2025 Whirlpool and GE stainless appliances. The spacious primary bedroom includes a nice walk-in closet and an ensuite bath, while the generous second bedroom comfortably accommodates up to two queen beds and boasts a full wall of closet space. Both updated bathrooms feature NEW cabinets, vanities, & fixtures, with glassed walk-in showers and recessed lighting. Brand NEW 2026 HVAC system and 2025 water heater. The unit also comes with its own assigned storage locker located just across the hall, ideal for storing all of your beach essentials. Conveniently located next door to the colorful shops and restaurants of Siesta Key Village, Whispering Sands is a premiere 55+ Gulf front property offering two heated pools, beachside Tiki Hut and gas grills, shuffleboard, canoe/kayak storage, and 800' of PRIVATE quartz sand beach. The clubhouse is currently undergoing complete remodeling. Upon completion in 2026, it will include a full catering kitchen, fitness rooms, large screen TV, and an elegant space for community wide or private social events. New landscaping plan for the building and throughout the entire 25-acre property is currently underway. Attractively priced below market, this unit represents a great investment. Don’t miss this opportunity to experience the ease of island living at Whispering Sands!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Harriet Stopher (404-316-8944)
4606 TIPPECANOE TRL #119, SARASOTA, FL 34233
$160,000220 Days on yellowkey MLS ID: A4671371
1 Days Off yellowkey (back on 5/6/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1258 Built: 1973Monthly Fee: $437 Tax: $882 (2024)Community: Lake TippecanoeCondo
Taxes:$882
Elementary School: Ashton Elementary
Remarks: Under contract-accepting backup offers. Brand New Price!! Welcome to Lake Tippecanoe — Sarasota’s Premier 55+ Community! This beautifully maintained 2-bedroom, 2-bath ground-floor condo offers 1,258 sq. ft. of comfortable, maintenance-free living in the heart of Sarasota. Step inside to an inviting open floor plan where the kitchen seamlessly flows into the great room—perfect for entertaining or relaxing. Natural light fills the spacious Florida room/dining area, overlooking a peaceful backyard setting. MOTIVATED SELLER Enjoy the convenience of indoor laundry and the ease of community living, with the association taking care of lawn maintenance, exterior upkeep (including the roof), pest control, cable, water, and trash pickup—so you can focus on enjoying the Florida lifestyle. Lake Tippecanoe is a well-established and friendly 55+ community featuring a clubhouse, social activities, and a serene lakefront setting. Ideally located near Sarasota’s world-famous beaches, top-rated golf courses, shopping, and dining, this condo offers the perfect blend of comfort, convenience, and community. Come experience the relaxed Sarasota lifestyle you’ve been dreaming of at Lake Tippecanoe!
Listing is courtesy of: JOHN HARDING REALTY (941-777-3007)
Listing Agent: Josh Mott (941-780-3063)
101 WHISPERING SANDS DR #301, SARASOTA, FL 34242
$449,00019 Days on yellowkey MLS ID: A4688898
REDUCED by $50,000 (10.0%) on 06/12/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1271 Built: 1969Monthly Fee: $1,483 Tax: $3,312 (2025)Community: Whispering SandsCondo
Taxes:$3,312
Remarks: Opportunity awaits in one of Siesta Key's most desirable GULF FRONT communities! Perfectly positioned on the 3rd floor of the popular Tropic View building just steps from the sugar white sands and turquoise waters of the Gulf, this 2 bedroom/2 bath Whispering Sands residence offers exceptional potential for the buyer with vision. The sellers are willing to offer a $30,000 SELLER CREDIT with an acceptable contract, to offset any future improvements or assessments. Ready for renovation and priced accordingly, this property serves as a blank canvas for updates and customization to suit your style. The spacious floor plan is complemented by a 34' screened and glass enclosed lanai that spans the entire length of the unit, providing additional valuable living space and a comfortable setting in which to relax or entertain year round. The primary bedroom includes a walk-in closet and ensuite bath with glassed shower. Equally spacious, the guest bedroom is large enough to accommodate two queen beds. Furnishings are negotiable. This unit also comes with an assigned storage locker on the same floor for all of your beach essentials. As one of Siesta Key's most sought after 55+ communities, Whispering Sands is known for its prime beachfront location, offering 800' of PRIVATE beach access, 2 heated pools, new beachside Tiki Hut, charcoal and gas grills, shuffleboard, beachside canoe/kayak storage, onsite management, and an active social atmosphere. Beach loungers are placed on the beach daily for the exclusive use of owners and their guests. The clubhouse is currently undergoing complete remodeling and will include brand new fitness equipment, a full catering kitchen, large screen TV, and an elegant, comfortable space for social events or private entertaining. Whispering Sands residents also enjoy a short stroll to Siesta Key Village's charming boutiques, restaurants, and entertainment while still enjoying the tranquility of Gulf front living. Whether you're seeking a seasonal escape, year round residence, or an opportunity to create a personalized coastal retreat, this property offers the prefect foundation in an exceptional location. Bring your imagination and discover the possibilities that await just moments from the Gulf!
4242 DRYDEN CIR, SARASOTA, FL 34241
$535,0008 Days on yellowkey MLS ID: A4696289
REDUCED by $14,000 (2.6%) on 06/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2324 Built: 1981Monthly Fee: $27 Tax: $2,992 (2025)Community: Bent Tree VillageSingle Family
Taxes:$2,992
Remarks: Virtually Staged. Experience stylish living in Sarasota's sought-after community of Bent Tree Village. This spacious 3-bedroom, 2-bath home offers convenient single-level living on a fenced homesite in desirable eastern Sarasota County. A welcoming entry garden creates a warm first impression, while the open and inviting floor plan seamlessly connects the main living areas, making the home ideal for both everyday living and entertaining. The generously sized primary suite features an ensuite bath and an oversized walk-in closet designed to accommodate even the most extensive wardrobe. Significant updates provide peace of mind, including a roof that is just four years old, enhanced with 18 inches of rodent-resistant insulation. Additional improvements include a newer HVAC system (2022), fresh interior and exterior paint, and upgraded gutters with 8-inch coverage along the rear of the home. The enclosed lanai, complete with durable epoxy flooring, offers the perfect space to relax or entertain year-round. Conveniently located just minutes from I-75, this home provides easy access to shopping, dining, downtown Sarasota, and the world-renowned beaches of Siesta Key and Florida's Gulf Coast. A one-year home warranty will be included with an acceptable offer.
Listing is courtesy of: ABUNDANT FIELDS REALTY LLC (941-302-1414)
Listing Agent: Summer Mcmillan (941-302-1414)
4060 WEBBER ST, SARASOTA, FL 34232
$329,50054 Days on yellowkey MLS ID: A4691042
REDUCED by $19,500 (5.6%) on 06/04/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1546 Built: 1960 Tax: $3,916 (2025)Community: Southern ViewSpa: NoSingle Family
Taxes:$3,916
Elementary School: Brentwood Elementary
Middle School: None
Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to 4060 Webber Street—an ideally located Sarasota home offering convenience, flexibility, and access to some of the area’s most sought-after outdoor amenities. Just moments from the Legacy Trail, the Sarasota Springs Trailhead, Downtown Sarasota, UTC, and world renowned beaches. This property is perfect for those looking to enjoy all that the Florida lifestyle has to offer. The home features a comfortable layout with inviting living spaces and plenty of natural light, enhanced by luxury vinyl plank flooring throughout the main living areas and primary bedroom for a clean, modern feel. The living room is anchored by a cozy wood-burning fireplace, creating a warm focal point for relaxing or entertaining. The spacious, open kitchen offers ample room for cooking, gathering, and hosting, making it the true heart of the home. The property features a fully fenced yard with a double gate on the side, providing direct access to a concrete pad—ideal for storing a boat, trailer, or additional vehicles. With no HOA restrictions, you’ll enjoy the freedom to make the most of your property without added limitations—whether for personal use or investment purposes. Located just a short drive to Siesta Key, downtown Sarasota, shopping, dining, and major roadways, this home combines accessibility with lifestyle appeal. Don’t miss this opportunity to own a versatile property in a prime central Sarasota location
Listing is courtesy of: HARRY ROBBINS ASSOC INC (941-924-8346)
Listing Agent: Derek Robbins (941-356-4906)
1750 BENJAMIN FRANKLIN DR #9F, SARASOTA, FL 34236
$1,500,000188 Days on yellowkey MLS ID: A4674543
REDUCED by $100,000 (6.3%) on 04/27/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 2035 Built: 1970 Tax: $9,743 (2024)Community: Key Tower SouthCondo
Taxes:$9,743
Remarks: Forever yours the unobstructed views of Sarasota Bay, Ringling Bridge and the Skyline of the City of Sarasota. Sip your morning beverage while watching the boats go by or dinner and the evening lights of the City. Beyond $200,000 has been invested to create this thoughtfully redesigned condo in floor to ceiling renovations to create this masterpiece with custom recessed lighting, porcelain flooring throughout, waterfall effect of quartz counters, contemporary sleek cabinetry designed kitchen, European spa-inspired Bathrooms designs and plumbed for your personal washer/dryer. Enjoy 2035 square feet of contemporary luxury in this light-filled 2-bedroom, 2-bath condominium with a versatile flex room currently used as a bedroom at Key Tower South directly on the soft quartz sands of the Gulf of Mexico on Lido Key. Expansive impact windows frame daily sightings of dolphins, seabirds, and shimmering water. Spa-inspired bathrooms feature premium fixtures. The open-concept floor plan offers excellent flow for entertaining or relaxed everyday living, enhanced by abundant storage and a flexible den ideal for a home office, 3rd bedroom or guest space. The building has recently undergone updates to its common areas, adding a fresh, modern aesthetic that complements the residence. Residents enjoy true beachfront living on Lido Key with immediate access to white sandy beaches and scenic waterfront walks. Just minutes away, St. Armands Circle offers world-class dining, boutique shopping, and vibrant coastal culture. This is a rare opportunity to own a luxury waterfront condo in Sarasota, perfectly positioned for both full-time living and seasonal enjoyment. Furnishings included with a few personal exceptions. Washer / Dryer hookup in the hall closet is ready for use.
Listing Agent: Midge Mccarthy (941-809-3800)
1750 BENJAMIN FRANKLIN DR #10G, SARASOTA, FL 34236
$1,175,000133 Days on yellowkey MLS ID: A4680259
REDUCED by $25,000 (2.1%) on 04/03/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1548 Built: 1970 Tax: $9,085 (2025)Community: Key Tower SouthCondo
Taxes:$9,085
Remarks: ****There is nothing left to do. Nothing to imagine. Completed in 2022, everything has been upgraded and transformed into the most modern luxury. This high-floor corner residence on Lido Beach in the Key South Tower building has been completely transformed—from ceilings to floors—into a home where every high-end creature comfort is already in place and water views unfold from every window. The building is so modern, so perfectly updated and completed that it even has its own hurricane/surge protection system surrounding the building-- unique and impressive. You must see this condo's extraordinary views in day and at night!!! ****Panoramic vistas stretch across the Gulf of Mexico, Sarasota Bay, the Ringling Bridge, and downtown Sarasota, creating a constantly shifting backdrop of light, water, and skyline. Set within a Lido Beach building that has already been elevated to the highest modern building standards, this residence offers peace of mind. The HOA’s abundant reserves reinforce the sense of security -- owners love living here. Inside, porcelain tile flows throughout, complemented by all-new ceilings and modern lighting that set a sophisticated, contemporary tone. ****The kitchen is both elegant and functional, featuring abundant new wood cabinetry, quartz countertops, and new appliances—designed for everything from casual mornings to elevated entertaining. The primary suite is a private sanctuary, framed by water views and finished with the finest luxury tile. It offers a walk-in closet, an ensuite bath with a walk-in shower, and thoughtful storage. The guest suite is equally impressive, with new tile, a walk-in closet, and beautiful views of the Intracoastal Waterway and downtown Sarasota. Spacious enough for a king bed, it also features its own walk-in shower, making it ideal for guests who appreciate comfort and privacy. ****Beyond the residence, Key Tower South has been fully reimagined, with the lobby and common areas completely renovated in 2025. Residents enjoy 220 feet of private Gulf frontage, a heated beachfront pool, expansive sundeck, direct beach access, saunas, a fitness room, library, bike storage, and on-site management—resort-level amenities without the crowds. ****This is not simply a condo. It is a fully realized beachfront lifestyle—elegant, effortless, and complete. Call now for a private showing. Prefer to experience it from afar? Drone footage and immersive fly-throughs are available.
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: Meredith Van Vaals (612-716-4784)
4401 LITTLE JOHN TRL, SARASOTA, FL 34232
$529,00011 Days on yellowkey MLS ID: A4695906
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1894 Built: 1986Monthly Fee: $50 Tax: $4,285 (2025)Community: Sherwood ForestSpa: YesSingle Family
Taxes:$4,285
Elementary School: Fruitville Elementary
Remarks: Nestled beneath majestic oak trees in the established Sherwood Forest community, this beautifully maintained home offers the perfect blend of privacy, character, and convenience. Situated on a spacious homesite, the property welcomes you with mature landscaping, abundant shade, and a tranquil setting rarely found in such a central Sarasota location. Inside, you'll find a thoughtfully designed floor plan featuring generous living spaces, abundant natural light, and comfortable accommodations for everyday living and entertaining. Brand new stainless steel appliances with a natural gas range. The home's layout flows seamlessly from the main living areas to the outdoor spaces, creating an inviting atmosphere for gatherings with family and friends. Step outside to enjoy the expansive yard, offering plenty of room for outdoor activities, gardening, or simply relaxing beneath the canopy of mature trees. Whether you're seeking a primary residence, seasonal retreat, or investment opportunity, this property provides exceptional flexibility and value. Conveniently located just minutes from I-75, shopping, dining, top-rated schools, golf courses, and Sarasota's world-famous beaches, this home combines peaceful neighborhood living with easy access to everything the Gulf Coast lifestyle has to offer. Don't miss this opportunity to own a charming Sarasota property in one of the area's most established and desirable communities. New HVAC
Listing is courtesy of: OSIPOV GROUP REAL ESTATE (941-284-4237)
Listing Agent: Bogdan Osipov (941-500-5885)
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