Location: Sarasota
Do Not Show Listings
199 WHISPERING SANDS DR #204, SARASOTA, FL 34242
$609,00094 Days on yellowkey MLS ID: A4684412
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1271 Built: 1970Monthly Fee: $1,579 Tax: $5,538 (2025)Community: Whispering SandsCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,538
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Welcome to effortless coastal living in this beautifully UPDATED second floor midrise residence in the premier GULF FRONT property of Whispering Sands! Designed with an OPEN CONCEPT floor plan, this light-filled condo showcases a bright, sophisticated 2023/2024 REMODELED kitchen featuring quartz countertops, stainless Samsung appliances, an impressive 8' breakfast bar with seating for 3, soft close cabinetry, and recessed lighting—all complemented by an elegant uplit tray ceiling. A true highlight is the expansive 29' x 8' lanai stretching the full length of the residence—offering an inviting extension of the living space ideal for relaxing, dining, or working from home, complete with hurricane impact sliders for total peace of mind. Both bathrooms have been tastefully updated with granite countertops and tiled, glass-enclosed walk-in showers, while ceiling fans and crown molding add comfort and sophistication throughout the unit. Beyond the residence, Whispering Sands offers true resort-style living in a premier Gulf front setting. Spend your days lounging on your private beach, taking a refreshing swim in one of two heated pools, an invigorating workout in the gym, or enjoying the vibrant social atmosphere of the clubhouse just steps from your door. Whether it’s a peaceful morning walk along the shoreline or a sunset gathering with neighbors, every day feels like a vacation. Perfectly positioned just steps from the clubhouse—currently undergoing complete remodeling in 2026—and pool, and a short stroll along the sidewalk to your 800' of your own private beach, this residence embodies the very best of resort style living. Ideally located just around the corner from the boutiques and restaurants of Siesta Key Village, you'll enjoy the perfect balance of relaxed beachfront living and easy access to dining, entertainment and island charm. Move right in and start enjoying the easy island lifestyle you’ve been dreaming of!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Harriet Stopher (404-316-8944)
1720 COUNTRY MEADOWS DR, SARASOTA, FL 34235
$355,0004 Days on yellowkey MLS ID: A4695223
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1321 Built: 1994Monthly Fee: $46 Tax: $3,808 (2025)Community: Country MeadowsSingle Family
Taxes:$3,808
Elementary School: Gocio Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Opportunity knocks in Sarasota! This lovely 3BD/2BA in Country Meadows featuring FRESHLY PAINTED interior with NEW CARPET, is conveniently located near UTC and The Meadows Country Club, with easy access to I-75 via Fruitville Rd or University Pkwy. This home features a split bedroom floor plan, stunning cathedral ceiling, eat-in space in kitchen and additional dining room space in an expansive great room, a primary bedroom suite with private en-suite bathroom and a very generous sized walk-in closet, interior laundry room, spacious 2-car garage, and fully enclosed lanai to enjoy morning coffee or evening dinners at sunset. Approximately 5 miles to Downtown Sarasota, 8 miles to St. Armands Circle/Lido Key, 11 miles to the award winning beaches on Siesta Key, and just 7 miles to Ringing Museum, Asolo Repertory Theatre, and SRQ airport for easy commuting. This well maintained home is competitively priced to sell. Don’t wait! Schedule your exclusive showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Elizabeth Mock (941-330-6200)
2312 GROVE ST, SARASOTA, FL 34239
$420,00047 Days on yellowkey MLS ID: A4690028
0 Days Off yellowkey (back on 4/20/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1449 Built: 1958 Tax: $1,447 (2025)Community: Blossom BrookSingle Family
Taxes:$1,447
Elementary School: Southside Elementary
Remarks: This 2 bedroom 2 bath home is in a great location near Siesta Key beaches, downtown, Sarasota Memorial and in the Southside School district. The home features a new roof installed in 2025, original terrazzo flooring in excellent condition and plenty of room for a pool. Surrounded by million-dollar homes and new builds, this property is ready for a refresh or bring your plans and build brand new. No HOA and a central Sarasota location make this a compelling opportunity for builders and buyers alike looking to capitalize on one of the city’s most promising markets. This 8750 square foot lot offers the ideal canvas for a custom home in a location experiencing significant redevelopment.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Jennifer Horne (941-773-0943)
430 BIRD KEY DR, SARASOTA, FL 34236
$2,150,00039 Days on yellowkey MLS ID: A4691206
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2498 Built: 1973Monthly Fee: $110 Tax: $22,378 (2025)Community: Bird Key SubSingle Family
Taxes:$22,378
High School: Pine View School
Middle School: Sarasota Middle
Remarks: This tastefully updated and remodeled single story home is ideally located within the sought after Bird Key neighborhood. Set on a large corner lot, it features a clean, contemporary style that feels both current and easy to live in. The home offers three bedrooms, two and a half bathrooms, and a two car garage, creating a comfortable and well balanced living environment. Inside, the open concept split floor plan provides both flow and definition, with separate living and family rooms suited to modern living. The remodeled kitchen features quartz countertops and sleek contemporary cabinetry and is centrally positioned to connect the main living, dining, and family spaces. Both living areas open through impact sliding glass doors to the lanai and pool, creating an easy transition between indoor and outdoor living. Fully opening sliders from the living and family rooms extend the space onto the pool deck, making the home particularly well suited for entertaining. The primary suite includes a spacious bedroom, walk in closet, and an updated en suite bathroom. Two additional guest bedrooms and a bathroom are located on the opposite side of the home, offering privacy for family and guests. The generously sized family room easily incorporates a small home office area. Recent improvements include a new tile roof in 2025, whole house propane generator 2025, a newer air conditioning system in 2023, and impact windows for added security and peace of mind. Bird Key offers one of Sarasota’s most desirable locations, just minutes from downtown Sarasota, St. Armands Circle, and Lido Beach. Residents also benefit from the nearby Bird Key Yacht Club, currently undergoing a full redevelopment and expected to reopen early in 2027 as a premier destination for boating, tennis, and social activities. PLEASE NOTE FRONT DOOR ENTRY IS LOCATED ON BOBWHITE WAY.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Yvette Sellyn (941-730-7756)
9620 CLUB SOUTH CIR #5107, SARASOTA, FL 34238
$289,000155 Days on yellowkey MLS ID: A4676320
REDUCED by $9,500 (3.2%) on 04/27/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1106 Built: 1995Monthly Fee: $605 Tax: $2,584 (2025)Community: Stoneybrook Clubside South 2Condo
Taxes:$2,584
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to a meticulously renovated within the last 4 years. Offered Turnkey Furnished, this 2 bed, 2 bath unit with an updated open-concept kitchen with granite counters and new soft close cabinet doors. The extended unique granite peninsula is a great eating/gathering area without the need for a separate table. This thoughtful design creates an airy feeling and a seamless flow to the Living Room and Lanai. The corner style lanai has which is very private, great to relax and enjoying nature and golfers from a distance. The lanai has new modern floor tile and protective Florida screen. The Primary Bedroom has a unique swivel mounted TV that can go from the Lanai to the primary in a moment. Both bathrooms have a new modern wall tile and soft close granite counter vanities. The master has a large walk-in closet, along with a stylish barn door for privacy. The seller recently updated washer, dryer and water-heater. The complex is getting new carports and storage sheds installed which the seller has paid for in full. Pickleball/tennis court and pool is nearby. Clubside South is a very active community with scheduled events and grill/gathering areas. A premier gated member-owned country club, Stoneybrook of Sarasota, is only a short distance from Siesta Key and offers easy access to shopping and borders the Legacy Trail. Ownership in Stoneybrook Golf and Country Club includes an updated clubhouse and restaurant, Har-Tru tennis facility, well-equipped fitness center and additional club pool and spa. Stoneybrook is nestled between Downtown Sarasota and Venice. In 2024, the Golf Course went through a complete redesign which is one of the top courses in Sarasota. This easy access first floor unit is unique, has the best reserved parking space in the community and a must see.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Kenneth Ipox (941-993-7279)
3356 PLANTATION PL, SARASOTA, FL 34231
$525,00019 Days on yellowkey MLS ID: L4961906
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1630 Built: 1982 Tax: $4,134 (2025)Community: South Pointe WoodsSingle Family
Taxes:$4,134
Remarks: Welcome to 3356 Plantation Place in beautiful Sarasota, Florida! This gorgeous 3-bedroom, 2-bathroom home with a 2-car garage has been completely remodeled from top to bottom with virtually everything brand new. Located in a highly desirable area just minutes from world-famous Siesta Key Beach, this move-in ready home offers modern style, quality craftsmanship, and peace of mind.Step inside to discover an open and inviting floor plan featuring brand new tiled floors throughout, fresh finishes, updated fixtures, and abundant natural light. The stunning remodeled kitchen showcases beautiful cabinetry, upgraded countertops, and modern finishes perfect for entertaining or everyday living. Both bathrooms have been tastefully renovated with stylish upgrades and designer touches.Major improvements include a brand new roof, new garage door, new doors and windows, new electric panel, new receptacles, and updated fixtures throughout the home. Every detail has been thoughtfully completed, making this property truly turnkey.Enjoy living in one of Sarasota’s most sought-after locations close to Siesta Key, shopping, dining, entertainment, parks, and top-rated schools. Whether you are looking for a primary residence, vacation home, or investment opportunity, this home checks all the boxes.This one won’t last long — schedule your private showing today!
Listing is courtesy of: HELLOSOLD LLC (954-778-5300)
Listing Agent: Dan Farber (954-778-5300)
5625 SOFT SKIES DR, SARASOTA, FL 34238
$534,900144 Days on yellowkey MLS ID: A4677533
REDUCED by $9,000 (1.7%) on 05/30/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2045 Built: 2020Monthly Fee: $268 Tax: $5,824 (2025)Community: Promenade Estates Ph 1Single Family
Taxes:$5,824
Remarks: Gorgeous 4-bedroom, 2.5-bath home built in 2020! This immaculate residence offers a generous open-concept floor plan featuring a spacious kitchen that flows seamlessly into the living and dining areas—perfect for everyday living and entertaining. A desirable split layout provides two guest bedrooms at the front of the home, along with a versatile flex room ideal for a den or home office. The expansive primary suite boasts dual walk-in closets, an oversized shower, and a relaxing garden tub. Upgraded large subway tile flooring runs throughout the home and is complemented by beautiful matching stone countertops. The kitchen is well appointed with stainless steel appliances, a walk-in pantry, and stylish cabinetry offering abundant storage. This home blends functionality with modern design and is located in a gated community featuring an impressive community center with a resort-style pool, basketball court, playground, sand volleyball court, and golf cart parking. Low HOA fees, no CDD, and no flood insurance required. Schedule your private showing today!
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Anthony Rudolph (702-286-5251)
5111 PEPPERMILL CT, SARASOTA, FL 34241
$425,000237 Days on yellowkey MLS ID: TB8432110
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1585 Built: 2002Monthly Fee: $275 Tax: $2,358 (2024)Community: Heritage Oaks Golf & Country ClubVilla
Taxes:$2,358
Tax Year: 2024
Remarks: Positioned within the lush, guard-gated fairways of Heritage Oaks Golf & Country Club, this beautifully appointed end-unit CLUBHOME style villa offers a rare blend of refined golf course living and exceptional privacy. Perfectly situated with no neighboring building on one side and tranquil water and preserve views beyond, this residence feels more like a private retreat than a typical villa residence. Offered furnished, this elegant two-bedroom, two-bath residence with a dedicated office/den and spacious two-car garage is designed for effortless Florida living. Sunlight pours through the open, airy floor plan, highlighting serene natural vistas and creating a warm, inviting ambiance throughout. The beautifully updated kitchen features granite countertops, stainless steel appliances, and a charming breakfast nook, seamlessly opening to the dining and living spaces designed for both everyday comfort and relaxed entertaining. The screened lanai becomes an extension of the home itself offring a peaceful outdoor sanctuary where mornings begin with tranquil preserve views and evenings unwind in complete serenity, far removed from the congestion often found in golf communities. Luxury vinyl flooring enhances the main living areas, while the spacious primary suite offers a walk-in closet, soaking tub, and glass-enclosed shower, creating a true retreat-like experience. Residents of Heritage Oaks enjoy an elevated country club lifestyle with championship golf, five heated pools, tennis courts, fitness center, clubhouse dining, and an active social calendar — all within one of the area’s most picturesque gated communities. Replumbed and re-piped, with a 2022 ROOF and 2017 A/C, this exceptional pet friendly CLUB home villa presents a rare opportunity to experience sophisticated golf course living without compromising privacy, tranquility, or comfort.
Listing is courtesy of: PREMIER SOTHEBY'S INTL REALTY (727-595-1604)
Listing Agent: Andrea Valdes (813-716-4843)
5125 WILLOW LEAF DR, SARASOTA, FL 34241
$1,190,00091 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
Elementary School: Lakeview Elementary
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)
5800 HOLLYWOOD BLVD #112, SARASOTA, FL 34231
$159,0004 Days on yellowkey MLS ID: A4695217
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 679 Built: 1976 Tax: $1,728 (2025)Community: Baywood Colony Garden AptsCondo
Taxes:$1,728
Remarks: Welcome to effortless Sarasota living at 5800 Hollywood Blvd—an inviting 1-bedroom, 1-bath condo ideally positioned for both comfort and convenience. This well-appointed residence offers a light and functional layout, perfect as a primary home, seasonal retreat, or investment opportunity—your chance to own a piece of paradise. Enjoy a relaxed coastal lifestyle just minutes from the world-renowned Siesta Key Beach, where powdery white sands and turquoise Gulf waters await. Everyday conveniences are at your doorstep, with an array of shopping, dining, and entertainment options nearby, creating the perfect balance of tranquility and accessibility. The interior offers a comfortable living space with a seamless flow, providing a welcoming environment to unwind or entertain. Whether you're enjoying a quiet morning or returning after a day at the beach, this residence delivers easy, low-maintenance living in a highly desirable location. An exceptional opportunity to own a piece of paradise in Sarasota at an attractive price point, close to everything that makes this area so sought after.
Listing Agent: Maryana Zilinskiy (941-744-6065)
5917 OLIVE AVE, SARASOTA, FL 34231
$473,0004 Days on yellowkey MLS ID: O6411402
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1330 Built: 1957 Tax: $3,209 (2025)Community: Golden AcresSingle Family
Taxes:$3,209
Elementary School: Gulf Gate Elementary
High School: Riverview High
Remarks: One or more photo(s) has been virtually staged. Located in the desirable coastal community of Sarasota, this inviting home offers a relaxed Florida lifestyle with a comfortable layout and bright, open living spaces. The interior features a functional flow designed for everyday living and easy entertaining, with well-sized bedrooms and versatile common areas. Outdoor space provides room to enjoy the warm weather year-round, whether relaxing, gardening, or hosting gatherings. Conveniently situated near Gulf beaches, shopping, dining, and cultural attractions, this property delivers both lifestyle and location in one of Sarasota’s most sought-after areas.
Listing is courtesy of: MAINSTAY BROKERAGE LLC (800-583-2914)
Listing Agent: Raquel Littlejohn (470-279-6333)
4204 PINE MEADOW TER, SARASOTA, FL 34233
$599,9004 Days on yellowkey MLS ID: A4694949
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2085 Built: 1978 Tax: $4,302 (2025)Community: Pine MeadowSingle Family
Taxes:$4,302
Elementary School: Ashton Elementary
Remarks: Welcome to 4204 Pine Meadow Terrace, a beautifully maintained home tucked away in the desirable Pine Meadow community of Sarasota. This inviting residence offers a spacious and functional layout with abundant natural light, comfortable living spaces, and a peaceful neighborhood setting. The home features a well-appointed kitchen, generous bedrooms, and a private outdoor area perfect for relaxing or entertaining with your salt water pool. Conveniently located near top-rated schools, shopping, dining, parks, and just a short drive to Sarasota’s world-famous beaches, this property combines comfort, convenience, and Florida lifestyle living at its best. Whether you’re searching for a primary residence, seasonal retreat, or investment opportunity, this home is a must-see. Roof is 2015, Hurricane windows and sliders 2018, HVAC 2021, Brand new septic pump, and Brand new kitchen appliances 2026
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Mark Singer (941-806-9121)
1023 TOCOBAGA LN, SARASOTA, FL 34236
$3,495,00011 Days on yellowkey MLS ID: A4694000
Bed: 3 Bath: 3.5 Gar: 4 Liv Area Sq Ft: 3599 Built: 1994Monthly Fee: $167 Tax: $27,942 (2025)Community: Tocobaga BaySpa: NoSingle Family
Taxes:$27,942
Remarks: Sophisticated gated living just moments from the heart of downtown Sarasota. Evoking the timeless elegance of Palm Beach with the warmth of Old Florida charm, this exceptional Spanish Mediterranean residence is tucked within the exclusive gated waterfront enclave of Tocobaga Bay. One of only 9 private residences in the community, ideally positioned just moments from Sarasota’s renowned dining, arts, shopping, and waterfront attractions. Surrounded by lush tropical landscaping and tranquil water views, the home is thoughtfully designed for both sophisticated entertaining and relaxed everyday living. Expansive interiors are filled with natural light, highlighted by a grand foyer, travertine flooring, oversized floor-to-ceiling picture windows, motorized shades, and custom window treatments throughout. The residence features 3 bedrooms, each with its own ensuite bath, along with a media room or private office and a private 3-stop elevator. The oversized 4-car garage offers exceptional storage and ample space for vehicles, golf carts, kayaks, and recreational equipment, while the air-conditioned bonus room provides flexibility for a fitness studio, game room, private office, or additional storage. The newly renovated chef’s kitchen is beautifully appointed with premium finishes including a La Cornue gas cooktop, Sub-Zero refrigerator, custom Campbell Cabinetry, spacious walk-in pantry, oversized center island and Taj Mahal quartz countertops and backsplash. The oversized living room offers an inviting atmosphere for gathering, while the separate formal dining room is perfectly suited for elegant dinners and entertaining. The primary suite serves as a peaceful sanctuary complete with its own Juliette balcony, dual custom walk-in closets, and a spacious ensuite bath. Two additional guest suites occupy the third floor, each with private baths, offering ideal comfort and separation for family and guest. Designed to embrace Sarasota’s indoor-outdoor lifestyle, the open-air heated saltwater pool is surrounded by lush tropical landscaping and expansive patio space for lounging and dining. Additional improvements: new tile roof (2023), new irrigation system (2024), updated water heaters (2023 & 2024), electrical panels (2024), and updated A/C units. Residents enjoy access to the community day dock with direct bay access, perfect for boating and waterfront enjoyment. Perfectly located near Sarasota’s renowned beaches, St. Armands Circle, The Bay Park, and the iconic Ringling Bridge, this remarkable residence offers an exceptional lifestyle just minutes from the energy and culture of downtown Sarasota. Offered fully furnished and ready for immediate enjoyment.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Linda Driggs (941-374-2920)
600 MOURNING DOVE DR, SARASOTA, FL 34236
$11,900,0004 Days on yellowkey MLS ID: A4694192
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 5767 Built: 2026Monthly Fee: $89 Tax: $47,243 (2025)Community: Bird Key SubSpa: YesSingle Family
Taxes:$47,243
Remarks: Under Construction. Positioned on one of Bird Key’s most expansive waterfront parcels featuring 200 foot of water-frontage, this extraordinary new construction estate captures sweeping Sarasota Bay views and represents a rare blend of architectural sophistication, enduring strength, and refined coastal luxury. Masterfully designed by renowned architect DSDG Architects and built by Dynan Construction, Sarasota’s premier waterfront builder, the residence has been thoughtfully engineered to the Fortified Gold standard, offering exceptional resilience and peace of mind for luxury waterfront living. A striking modern façade introduces interiors defined by dramatic floor-to-ceiling glass, allowing natural light and panoramic water views to pour throughout the home while seamlessly blending indoor and outdoor living. Warm, curated interior finishes create an inviting yet sophisticated ambiance, balancing contemporary architecture with timeless livability. Designed for both grand-scale entertaining and effortless daily living, the residence features four luxurious bedroom suites, a private office, a gym/wellness center with sauna, elevator access to all levels, an expansive rooftop deck designed to capture breathtaking sunsets over Sarasota Bay, and a spacious three-car garage. The outdoor living experience is equally compelling, with resort-inspired entertaining spaces thoughtfully designed to embrace the coveted waterfront lifestyle. The masterfully designed infinity-edge pool serves as the centerpiece of the outdoor living experience, offering a striking visual connection to the surrounding waterfront setting. Set within one of Sarasota’s most prestigious waterfront communities, this exceptional offering presents a rare opportunity to own a statement residence between downtown Sarasota and St. Armands Circle, offering an unmatched lifestyle surrounded by fine dining, boutique shopping, cultural attractions, boating amenities, and breathtaking Gulf beaches.
Listing is courtesy of: COASTAL RESERVE (941-586-7736)
Listing Agent: Cassandra Miller (941-586-7736)
6157 MIDNIGHT PASS RD #F22, SARASOTA, FL 34242
$529,9004 Days on yellowkey MLS ID: A4692762
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1332 Built: 1974 Tax: $5,274 (2025)Community: Bay OaksSpa: YesCondo
Taxes:$5,274
Remarks: This property is a rare find, featuring two master suites upstairs, each with its own private balcony. The home is tastefully decorated and is being sold Turnkey, making it an excellent opportunity for immediate use or investment. Notably, the property already has a strong track record of rental income with several future bookings already in place. The Bay Oaks community offers a serene setting with mature landscaping and a wide array of amenities, including a heated pool, tennis courts, recreation room and a fishing pier. It also provides the convenience of on-site management and a picnic area with Barbeques for your enjoyment. Located less than a mile from Crescent Beach, the property offers easy access to the world-renowned powdery, quartz sand of Siesta Key, recently ranked as the #4 beach in the world by Tripadvisor in 2025. The area is a premier destination spot. Additionally, the trolley stops directly in front of the complex providing easy transportation to the various dining, shopping and nightlife options Siesta Key is famous for.
Listing is courtesy of: BECKMANN REAL ESTATE (941-346-3500)
Listing Agent: Josh Beckmann (941-321-3500)
3360 RAMBLEWOOD DR S #8, SARASOTA, FL 34237
$174,90015 Days on yellowkey MLS ID: A4693442
REDUCED by $5,000 (2.8%) on 05/28/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1003 Built: 1974Monthly Fee: $605 Tax: $631 (2025)Community: Ramblewood AcresCondo
Taxes:$631
Elementary School: Tuttle Elementary
Remarks: Price Reduction & Seller Now Offering 6 Months of HOA Fees Paid Upfront!!! Welcome to this clean and cozy 2-bedroom, 2-bath detached villa that combines the privacy and charm of a single-family home with the ease of maintenance-free villa living. Nestled in the desirable southeast corner of Ramblewood Acres, this home features its own garden area and backyard retreat—perfect for relaxing, entertaining, or creating your own tropical oasis. Move-in ready as-is, or use it as a blank canvas for a full renovation to suit today’s modern style and finishes. Residents of Ramblewood Acres enjoy an exceptional lifestyle with amenities for all ages, including: 3 swimming pools, tennis courts, playground and clubhouse with fitness facilities. Prime Location, just minutes from Downtown Sarasota, St. Armands Circle, Lido Beach, and Sarasota Bradenton International Airport, this community offers the perfect combination of comfort, recreation, and convenience. Some photos are Virtually Staged in order for you to see the home's full potential.
Listing is courtesy of: ALBERT WOOSTER & COMPANY (941-350-1220)
Listing Agent: Kimberly B. Wolf (941-302-0034)
4021 OLIVE AVE, SARASOTA, FL 34231
$435,000210 Days on yellowkey MLS ID: A4670598
0 Days Off yellowkey (back on 5/19/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1560 Built: 1988 Tax: $4,820 (2024)Community: Flora-VillaSingle Family
Taxes:$4,820
Remarks: Under contract-accepting backup offers. Welcome to this spacious 3-bedroom, 2-bathroom home in beautiful Sarasota. Step inside and you’ll find an open, inviting floor plan filled with natural light and plenty of room for both relaxation and entertaining. Each bedroom is generously sized with ample closet space, offering both comfort and functionality. The kitchen flows seamlessly into the living and dining areas, making gatherings easy and enjoyable. The large second-story loft provides a flexible space—perfect for a home office, media room, or guest retreat. The home’s outdoor space is just as impressive, featuring a spacious backyard ideal for hosting, gardening, or adding your own personal touch. Tucked within a quiet cul-de-sac, the location offers an extra layer of privacy and peace while still being close to everything Sarasota has to offer. This property has also been successfully used as a short-term rental, making it a great option for investors or those seeking flexible ownership. With its proven rental history, it’s ready to continue generating income or become your personal retreat. Just minutes from some of America’s best beaches, you’ll have easy access to Sarasota’s stunning coastline and turquoise waters. Nearby, you’ll also find a wide array of shopping, dining, and entertainment options to enjoy year-round. Whether you’re looking for a primary residence, vacation home, or income-producing investment, this Sarasota gem delivers comfort, convenience, and opportunity.
Listing Agent: Spencer Robinson (941-702-0365)
5214 BEECHMONT AVE, SARASOTA, FL 34234
$180,00093 Days on yellowkey MLS ID: A4684037
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1060 Built: 1973 Tax: $2,497 (2025)Community: Tri-Par EstatesSpa: YesMobile Home
Taxes:$2,497
Remarks: Tri-par Estates in an active, vibrant 55+ community where each property is individually owned with a deed and title to the home. This large corner lot is NOT in the flood zone, but IS in the pet-friendly area and the homes comes furnished. The open living/dining combo is spacious and bright with updated windows, mostly 2025- low-e/double-pane. Other updates include vinyl planking floor throughout, kitchen, bathrooms, all appliances newer including water heater, and freshly painted throughout. The main washroom features a step-in shower, and the primary ensuite has a tub with shower. The laundry is located inside the home for your easy convenience. Public records indicate 880 sq ft for the main house; a mini-split unit has been added to the all-season Florida room for a total of 1,060 sq ft. Outside updates include: TPO roof- 2025, aluminum carport - 2026, pavers -2025, electrical box, garden sprinkler system, and addition of a 10' x 14' shed which provides tons of space for all your storage needs. Tri-par provides a wealth of amenities: enjoy the heated/cooled Olympic-sized for year round swimming, newly constructed large hot tub, palapa tiki hut, pickleball courts, fitness center, shuffleboard courts, miniature golf, horseshoes, game rooms for ping-pong, billiards and more. The clubhouse is host to events such as dinners, dances, and celebrations of all kinds. Situated only minutes from downtown Sarasota, museums, shopping, eateries, the airport and of course the world-renowned Siesta Key and Lido key beaches! You own your own land in this special parks and recreation district, and pay no HOA fee directly to the association. The annual amount of $1,648 is included in your property taxes, and includes such items as fiber-optic internet and direct TV- many channels. Golf cart-friendly community with optional storage for your R/V or boat.
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Ivy Neyedly, Pllc (941-914-1994)
1755 7TH ST, SARASOTA, FL 34236
$2,100,00046 Days on yellowkey MLS ID: GC539589
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4451 Built: 2023 Tax: $32,680 (2025)Community: Schindler SubHalf Duplex
Taxes:$32,680
Remarks: A rare blend of modern luxury, income potential + lifestyle flexibility awaits in this striking custom 2023 duplex in the heart of Gillespie Park, moments from downtown Sarasota. Designed for those wanting more than just a home, this architectural standout offers 4,400+ sq ft of elevated living with two fully independent residences, each approx 2,200 sq ft featuring 2 bedrooms, 2 bathrooms, private laundry, soaring ceilings + a light-filled expansive design. Whether downsizing, creating a multi-gen retreat, or offsetting your lifestyle with income, this property delivers exceptional versatility, live in one + generate revenue from the other (currently $3,600/month). The main level showcases a chef-inspired kitchen with premium Thermador appliances, gas cooking, dual dishwashers, walk-in pantry + built-in coffee/wine bar, while the upper level offers a refined private living experience with sleek Bosch appliances+ ensuite bedrooms. Outdoor living feels like a private resort with a secluded courtyard featuring an outdoor kitchen and hot tub, plus an expansive second-level balcony ideal for relaxing. Built for efficiency + longevity with solar power, natural gas tankless water heaters, elevator access + rare 3-car alley-access garage, features seldom found this close to downtown. Zoned for short-term rentals and crafted as a high-end multigenerational retreat with full custom handicap-accessible design, delivering an exclusive lifestyle in a prime location.
Listing is courtesy of: DANIEL CRAPPS AGENCY, INC. (386-755-5110)
Listing Agent: Daniel Crapps (386-397-3002)
5102 MOELLER AVE, SARASOTA, FL 34233
$369,90028 Days on yellowkey MLS ID: A4691946
REDUCED by $15,100 (3.9%) on 05/20/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1744 Built: 1992Monthly Fee: $23 Tax: $3,439 (2025)Community: Cedar Grove Of 1St Add ToSingle Family
Taxes:$3,439
Middle School: McIntosh Middle
Remarks: Welcome to one of Sarasota’s best valued opportunities for First time home buyers, and Investors looking for flexible living space in a Prime Location in a very desirable school district. With approximately 1,775 square feet of living space, this meticulously maintained 2-story home offers room to grow with 3 spacious bedrooms, 2.5 bathrooms, and a versatile office/flex space perfect for working from home, hobbies, a guest area, or additional functional living space. Located at the end of a quiet street with minimal traffic, the home offers a more peaceful setting where you can ride bikes, play outside, and families can enjoy a neighborhood feel that’s becoming harder to find. Even better, Ashton Elementary School and Sarasota Middle School are within walking distance, allowing kids to walk to school just steps away. The fully fenced backyard and beautiful wood decking create the perfect space for pets, entertaining, or relaxing outdoors. Inside, the bright open kitchen features granite countertops, light wood cabinetry, and an inviting layout designed for everyday living and gatherings. One of the biggest advantages of this home is convenience. Shopping, restaurants, I-75 access, and Sarasota’s world-famous beaches are all only minutes from your door. With rising Sarasota prices making larger homes harder to find at this price point, this property offers a rare combination of space, flexibility, location, and value.
Listing Agent: Judi Taulbee (941-544-6227)
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