Location: Sarasota
Do Not Show Listings
1504 S LODGE DR, SARASOTA, FL 34239
$6,990,00044 Days on yellowkey MLS ID: A4683855
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 5450 Built: 1965Monthly Fee: $25 Tax: $15,432 (2025)Community: Cherokee LodgeSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$15,432
Elementary School: Southside Elementary
High School: None
Tax Year: 2025
Middle School: None
Remarks: First time available in 40 years! "Tween Bridges" is a rare bayfront property located in highly sought-after Cherokee Park, West of Trail. This 4-bedroom,3.5 bath residence offers unobstructed panoramic views of Sarasota Bay. The breathtaking sunsets and stunning vistas of Ringling Bridge, Siesta Key and downtown are truly mesmerizing. Boating enthusiasts will appreciate the brand-new dock with a 16,000lb lift and direct access to Sarasota's exceptional boating waters. Enjoy the home as it is or take advantage of this rare opportunity to build a custom waterfront estate on this magnificent property. Offered at $6,990,000, do not miss your chance to own one of Sarasota's finest waterfront locations. "Tween Bridges" is named for its location between The Ringling Bridge and The Siesta Key north bridge.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Melody Davis (908-202-4085)
9610 CLUB SOUTH CIR #4106, SARASOTA, FL 34238
$249,00064 Days on yellowkey MLS ID: A4682812
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1106 Built: 1995Monthly Fee: $571 Tax: $2,184 (2025)Community: Stoneybrook Clubside South 1Condo
Taxes:$2,184
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Middle School: Laurel Nokomis Middle
Remarks: Welcome to the resort style living at its finest in Stoneybrook Golf & Country Club, where luxury, leisure, and an active lifestyle come together in one exceptional community. Located within the desirable Clubside South enclave, residents enjoy their own private tennis and Pickleball courts, a heated pool with screened lanai, outdoor kitchen, grilling area, along with an assigned carport and storage closet for each residence. Beyond the neighborhood amenities, the club itself offers an unparalleled country club experience. Golf enthusiasts will appreciate the beautifully renovated 18-hole championship course designed by renowned architect Kipp Schule’s. Additional world class amenities include lighted Har Tru tennis courts, Pickleball courts, a pro shop, state of the ar fitness center, bocce courts, putting greens, driving range, an additional heated pool and spa, and a full service restaurant and bar with catering services. Scenic walking and biking trails, fishing opportunities, and a vibrant calendar of social activities including yoga, Mah-Jongg, line dancing, and more, create a Tru resort lifestyle year round. This beautifully furnished two bedroom, 2 bath residence is ideally situated on the ground floor, offering effortless access and breathtaking views of the lush golf course and sparkling lake. The highly sought after first floor location, combined with the tranquil scenery and turnkey furnishings makes this an outstanding opportunity to own in one of the area’s most desirable golf and country club communities. Perfectly located in Sarasota, this home is minutes from the vibrant dining, Art’s, and shopping of downtown, the upscale boutiques and restaurants of St Armand’s Circle, and the area’s world renowned Gulf Coast beaches, including the powder white sands of Siesta Key Beach. A perfect seasonal retreat, full time residence, or investment, this exceptional condo delivers comfort, convenience, and an unbeatable lifestyle.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Jennifer Bright (941-320-4989)
750 N TAMIAMI TRL #314, SARASOTA, FL 34236
$439,900107 Days on yellowkey MLS ID: A4676869
Bed: 2 Bath: 1.0 Gar: 2 Liv Area Sq Ft: 1085 Built: 2001Monthly Fee: $1,117 Tax: $5,186 (2025)Community: Renaissance 1Spa: YesCondo
Taxes:$5,186
Elementary School: Alta Vista Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Welcome to Renaissance residence 314, a blend of charm and modern luxury in this fully renovated condominium offering over 1,000 square feet of thoughtfully designed living space. This beautifully updated unit features an expansive family and dining room, an oversized primary bedroom, and a versatile den that can easily serve as a second bedroom. Completely renovated in 2024, this home is move-in ready with every detail meticulously updated for your convenience. The sleek kitchen boasts matching GE Profile appliances, an LG washer and dryer, and new cabinetry with built-in storage solutions, offering ample space for all your needs. Freshly repainted in a neutral palette and paired with new luxury vinyl flooring throughout, the space provides a timeless foundation for any design style you choose. The spacious primary bedroom includes custom built-in closets and offers plenty of room to craft your ideal Sarasota retreat, while the remodeled en-suite bath features elegant quartz countertops, new cabinetry and a stunning shower with dual showerheads, exuding style and comfort. Renaissance is more than just a residence, it’s a lifestyle. This 16-story condominium high-rise offers an impressive array of resort-style amenities, including beautifully landscaped plazas and fountains, 24-hour front desk service and keycard secured entry. The building’s proactive maintenance ensures peace of mind, with recent updates including a new roof and cleaned piping systems in 2024. Designed with durability in mind, Renaissance features reinforced concrete beams, fireproof materials, and elevated guest parking and lobby spaces, providing stability and security. Residents enjoy world-class amenities such as a clubroom, business center, fitness center, resident theater and concierge services. For hosting guests, the building offers two fully equipped guest suites available by reservation. This unit comes with two assigned parking spaces conveniently on the third floor of the secured garage, ensuring your vehicles are protected and elevated over 50 feet above sea level. In the heart of Sarasota’s vibrant cultural district, Renaissance places you near The Bay Park and the city’s dynamic social scene. Designed in the style of an Italian villa, the building's charm is matched by its prime location, where water views are preserved thanks to Renaissance's ownership of aerial rights over the park. Embrace the luxury, convenience and unmatched beauty of living in Renaissance Unit 314. Your Sarasota dream home awaits!
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Moriah Taliaferro (941-504-9910)
7150 N TAMIAMI TRL #S-614, SARASOTA, FL 34243
$95,00049 Days on yellowkey MLS ID: A4684819
REDUCED by $14,000 (12.8%) on 04/13/2026
Bed: 0 Bath: 1.0 Liv Area Sq Ft: 348 Built: 1959Monthly Fee: $760 Tax: $2,005 (2024)Community: Sarasota Cay Club CondoSpa: NoCondo
Taxes:$2,005
Elementary School: None
Tax Year: 2024
Remarks: Enjoy your getaway with the full hotel experience at the Ramada Inn, complete with a huge heated pool, World Famous Tiki Bar & Grill, Live music, and an arcade all just steps from your door. This adorably updated room has everything you need for a relaxing beach vacation or a comfortable extended stay. Perfect for families, business travelers, or solo guests seeking convenience and comfort. Secure parking, and Marina access with boat rentals available. Sleeps up to 5 guests, with one queen bed and one bunk bed. Great location, close to beaches, downtown Sarasota, Sarasota Airport and St Armand's Circle.
7150 N TAMIAMI TRL #S-612, SARASOTA, FL 34243
$95,00049 Days on yellowkey MLS ID: A4684634
355 CALLE MIRAMAR, SARASOTA, FL 34242
$3,500,00096 Days on yellowkey MLS ID: N6142420
Bed: 6 Bath: 0.0 Gar: 2 Liv Area Sq Ft: 2660 Built: 1993 Tax: $25,782 (2025)Community: Sarasota BeachSpa: YesApartment
Taxes:$25,782
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Middle School: Brookside Middle
Remarks: Rare opportunity to own a pristine, income-producing duplex just steps from Siesta Key Village and one block from the powdery sands of Siesta Key Beach—recognized as one of the finest beaches in the world. Properties offering this level of condition, location, and flexibility are seldom available. Each residence features 3 bedrooms and 2.5 bathrooms and has been thoughtfully renovated and fully furnished for immediate enjoyment or turnkey rental use. Interiors showcase luxury vinyl flooring throughout, updated kitchens, split-bedroom layouts, in-unit laundry, and large flat-screen televisions in all bedrooms and living areas—designed to support both comfortable living and strong rental demand. Bright, sunfilled open bedrooms with generous closets complement spacious, well-appointed kitchens. Outdoor living is exceptional, with 2 heated private pools and spas, front and rear patios, and deeded canal access just around the corner—features that enhance both lifestyle enjoyment and guest appeal. Each unit includes a private garage with game room, accommodating up to two vehicles, along with additional driveway parking—an exceptional convenience on Siesta Key. The property offers outstanding versatility, whether used as a primary or seasonal residence with supplemental rental income, or operated as a dual-income investment. Significant exterior improvements include updated siding and trim, hurricane-rated windows on the front elevation, refreshed lighting, fresh exterior paint, and brick paver driveways and walkways—creating a polished coastal offering in one of Siesta Key’s most desirable and supply-constrained locations.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Matthew Vander Wyden (941-483-0977)
7885 MAINSAIL LN, SARASOTA, FL 34240
$1,795,00068 Days on yellowkey MLS ID: A4682351
4 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2487 Built: 2022Monthly Fee: $500 Tax: $17,017 (2024)Community: Shoreview At Lakewood Ranch WatersideSpa: YesSingle Family
Taxes:$17,017
Remarks: Under contract-accepting backup offers. This beautifully appointed three-bedroom, three-bath plus den custom Pulte Pinnacle model showcases refined design, thoughtful upgrades, designer touches, and serene waterfront living in the highly desirable Shoreview community of Waterside. From the moment you arrive, the striking stone front façade, manicured landscaping and elegant glass entry door create a sophisticated first impression. Inside, tile flooring flows seamlessly throughout the home, complemented by modern designer lighting, stylish ceiling fans, tray ceilings, crown molding and curated architectural accents that elevate every space. The open-concept floor plan is designed for effortless entertaining and comfortable everyday living. The spacious great room features tray ceilings and pocketing sliding glass doors that fully open to the oversized lanai, blending indoor and outdoor living while framing stunning lake views. The adjacent dining area is positioned to enjoy natural light and water vistas, while the chef’s kitchen serves as the heart of the home with KitchenAid and Whirlpool appliances, sleek cabinetry, and a large eat-at bar ideal for gatherings and casual dining. Go outside to your private Florida retreat where an expansive screened lanai overlooks tranquil water views. The heated saltwater pool and spa are set against a panoramic screen enclosure, creating a breathtaking backdrop of shimmering lake views. An outdoor kitchen enhances the space, making it ideal for alfresco dining and entertaining year-round. The primary suite is a peaceful sanctuary featuring a tray ceiling, large picture window overlooking the pool and lake, and a beautifully appointed spa-inspired bath with a spacious walk-in shower and refined finishes. One guest bedroom with stunning window-filled bump-out offers its en-suite bath, while the second guest bedroom is serviced by a dedicated full bath, providing privacy and comfort for family or visitors. The private den, accessed through double doors, features a tray ceiling and built-in designer cabinetry, ideal for a home office, library or creative space. Additional highlights include hurricane-rated windows for peace of mind, a spacious three-car garage with ample storage and meticulous landscaping that enhances the home’s curb appeal. In Shoreview at Waterside, residents enjoy a resort-inspired lifestyle with access to a stunning clubhouse, state-of-the-art fitness center, resort-style pool and spa, tennis and pickleball courts, dog parks, playground and scenic walking trails along Kingfisher Lake. Waterside offers charming waterfront dining, boutique shopping, vibrant community events and picturesque views throughout the area, creating a dynamic yet peaceful setting. This exceptional residence offers a blend of luxury, comfort and community in one of Lakewood Ranch’s sought-after neighborhoods.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-907-9541)
Listing Agent: Laura Stavola Pllc (941-447-4875)
6415 MIDNIGHT PASS RD #705, SARASOTA, FL 34242
$584,50063 Days on yellowkey MLS ID: A4683086
REDUCED by $15,300 (2.6%) on 04/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1287 Built: 1975 Tax: $3,669 (2025)Community: AnchorageSpa: NoCondo
Taxes:$3,669
Remarks: Welcome to the best location on Siesta Key. The Anchorage is located on the corner of Stickney Point and Midnight Pass. It’s all about convenience and living the good life. Walk to bars, restaurants, the beach. You can walk across the street and rent a boat. Speaking of boats you can dock your boat on our giant seawall for $10.00... yes...ten dollars a month. Your new condominium is an open floor plan with living room/dining room combo. All three rooms have hurricane sliding doors. The main bedroom is very large and the master bath has a walk-in shower. The guest bedroom has 2 double beds with a tub/shower! You also have one covered parking space underneath the main building valued at $25,000.00. We have a beach easement to Siesta Key beach! Our Seawall was replaced in 2019. The building and grounds are in wonderful shape! The Anchorage has so many amenities to offer owners and renters, including an Olympic-size heated swimming pool, Fitness Center, Lighted Pickleball & Tennis Courts, Clubhouse, BBQ & Picnic Areas and Kayak Storage! There is a trolly that you could take to Siesta Key Village to enjoy more shopping, entertainment and dining options. The Anchorage is very conveniently located near Stickney Point Bridge to give you easy access to the mainland, including downtown Sarasota!
Listing is courtesy of: DELUCA REALTY INC (941-487-7162)
Listing Agent: Anthony Deluca (941-685-6001)
2280 MIDNIGHT PEARL DR, SARASOTA, FL 34240
$475,00023 Days on yellowkey MLS ID: N6143658
REDUCED by $10,000 (2.1%) on 04/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1844 Built: 2019Monthly Fee: $124 Tax: $3,509 (2025)Community: Bay LandingSingle Family
Taxes:$3,509
Elementary School: Tatum Ridge Elementary
Middle School: McIntosh Middle
Remarks: Welcome to 2280 Midnight Pearl Dr, a beautifully designed and maintained one-story home offering comfort, functionality and modern style. Built with durable all-concrete block construction, this residence features a truly open-concept layout perfect for both everyday living and entertaining. At the heart of the home, a spacious kitchen with a large island overlooks the dining area, great room and cozy breakfast nook, creating a seamless flow of living space. From here, step out onto the covered lanai and enjoy the screened back porch—ideal for relaxing or hosting guests year-round. A sun tunnel skylight fills the home with natural light, helping reduce the need for artificial lighting during the day and contributing to lower power bills. The owner’s suite is thoughtfully positioned at the rear of the home, providing optimal privacy along with an ensuite bath. Two additional bedrooms are located at the front and share a full bathroom, making this layout ideal for families or guests. Convenience meets practicality with a laundry room just off the garage, functioning perfectly as a mudroom entry into the kitchen. The home also comes equipped with stainless steel appliances, including a dishwasher, range, refrigerator and microwave. Residents enjoy a low HOA fee of just $124 per month, which includes access to a beautiful heated community pool and fitness room. Additional updates include a newly replaced roof in September 2025, offering peace of mind for years to come. Ideally located with easy access to I-75, this home is just a short drive from Sarasota’s world-famous beaches, shopping, dining and top-rated schools. This well-maintained home combines modern features with a smart layout in a spectacular and convenient location—ready for you to move in and enjoy.
Listing is courtesy of: PELICAN REALTY CORP (941-270-2650)
Listing Agent: Anna Bridinger, Pa (941-544-8195)
631 N ORANGE AVE #208, SARASOTA, FL 34236
$344,900166 Days on yellowkey MLS ID: A4671326
REDUCED by $10,000 (2.8%) on 04/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 784 Built: 1982 Tax: $2,508 (2024)Community: Mentone CourtSpa: NoCondo
Taxes:$2,508
Remarks: One or more photo(s) has been virtually staged. Unit #208 is one of just five 2BR/2BA homes for sale under $500,000 in the entire SRQ downtown region – it’s the only one under $399,000 and it’s the closest to the downtown center. Located In the charming Mentone Court complex with just 16 residences in the heart of the Rosemary District, the entire complex is above the flood plain and #208 has assigned covered parking. Its HOA fees and taxes may be the lowest in city and the HOA pays for insurance on the building, a huge benefit. With a walkability score of 92 it’s a "Walker's Paradise” and four restaurants with outdoor dining are less than a block away in gorgeous Citrus Square which has its own Veo Public Scooter stand. Walk five-minutes to the Main Street dining scene, or a few blocks to Whole Foods. It’s all about affordable convenient city living. This bright, well laid-out 2nd floor corner unit feels spacious with high ceilings, an open floor plan and large-format porcelain tile, and five closets. Recessed ceiling lighting shows off a fresh tropical paint color palette, the plantation blinds on all windows and the 12’ slider’s vertical blinds are included. The kitchen’s refinished solid wood cabinetry complements granite countertops while under-cabinet lighting illuminates a striking pearlescent subway tile backsplash. The induction range, dishwasher and refrigerator are new (never used). Also new is the efficient HVAC system and four Hunter remote-control ceiling fans. Two updated baths feature a pristine cast iron tub in one and an oversized shower with classic white subway tile in the other. A stacked washer/dryer is included. The large primary bedroom can fit a king bed and has a California-style walk-in closet. The 12’ glass slider opens to an oversize screened-in lanai protected by a motorized 12’ roll-down Kevlar storm/sunshade rated for a Cat. 5 hurricane. This top-quality screen has a battery backup and its MagnaTrack keeps it taut – no sagging, ever. A remote control lets it double as a sunscreen to use the patio throughout the Summer. Master insurance on the structure, water, sewer, trash, reserve funding, landscaping and exterior maintenance are all included in the low $522 monthly HOA fee. The HOA is professionally managed and fully funded; no special assessments are planned. Minimum one-week rentals and small pets are allowed. Mentone Court is not in a flood zone has never had storm damage – block construction with a newer tile roof means it’s inexpensive to insure appliances and contents as the building is insured by the HOA for peace of mind. Under three stories it’s exempt from Milestone inspections, rules and high mandated reserves. The Legacy Trail starts in Payne Park, a one mile bike ride away. Longboat Key is a short drive or just grab the nearby free Bay Runner trolley that runs daily every twenty minutes 7am–11pm to St. Armands Circle, then to Lido Beach Park with its huge pool and amenities then on to unspoiled South Lido Beach with its nature walks, see the photos. It’s the same pristine white sand as Siesta Key 1000 feet to the south, but without the crowds, traffic and parking hassles. Unit #208 checks off every box for worry-free affordable downtown living with easy beach access. With its own covered parking spot and only 12-minutes by Uber to the airport, Unit #208 could be your seasonal 2nd home, investment property that pays for itself, or live full-time downtown and walk everywhere.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
631 N ORANGE AVE #107, SARASOTA, FL 34236
$389,900274 Days on yellowkey MLS ID: A4659021
REDUCED by $10,000 (2.5%) on 04/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 784 Built: 1982 Tax: $2,713 (2024)Community: Mentone CourtCondo
Taxes:$2,713
Remarks: This beautifully renovated first-floor unit is one of just five 2BR/2BA homes for sale under $500,000 in the SRQ downtown region – and it’s the closest to the downtown center with a five-minute walk to the Main Street dining scene and shops, or a few blocks to Whole Foods. Located in the charming Mentone Court complex with just 16 residences in the heart of the Rosemary District, the entire complex is above the flood plain and #107 has assigned covered parking just 50 feet away. Its HOA fees and taxes may be the lowest in city and the HOA pays for insurance on the building. With a walkability score of 92 it’s a "Walker's Paradise” and four restaurants with outdoor dining are less than a block away in gorgeous Citrus Square which has its own Veo Public Scooter stand. The oversize lanai leads directly to private green space, then to a locking gate in the garden wall and on to four restaurants in Citrus Square just 400 feet away. Main Street’s cafes & shops are a five-minute walk, while Whole Foods is a few blocks away. #107 comes furnished with a 75" Frame TV, all the artwork and most of the furniture pictured. Gut-renovated and unoccupied since (new plumbing, paint, AC/heat, ceiling fans). The unit feels spacious with high ceilings, porcelain tile flooring, 5" baseboards, plantation blinds and four closets. The guest shower is oversized, and the primary bath has a 3/8” frameless glass shower door; both have high-end Kohler Awaken fixtures, Choreograph shower barres and gorgeous designer tile. The new LG heat pump washer/dryer is ready for your beach towels. The kitchen features new Samsung smart Wi-Fi appliances with an induction range and quiet dishwasher. Quartz countertops complement solid hickory dovetailed cabinets that will never delaminate. The backsplash and island are clad with chic hand-made Moroccan Zellige tile by Cle. The oversized 5'x13' lanai (with storage closet) is protected by a 12' motorized roll-down Kevlar storm/sunshade rated for a Cat. 5 hurricane; its MagnaTrack system keeps the screen taut – no sagging, ever. It doubles as a sunscreen so you can use the patio year-round. Master insurance on the structure, water, sewer, trash, reserve funding, landscaping and exterior maintenance are all included in the low $522 monthly HOA fee. All you pay is cable and electricity. The HOA is professionally managed and fully funded; no special assessments are planned. Minimum one-week rentals and small pets are allowed. Community is not in a flood zone has never had storm damage – block construction with a newer tile roof means it’s inexpensive to insure the contents. Under three stories it’s exempt from Milestone inspections, rules and high mandated reserves. The Legacy Trail starts in Payne Park, a one mile bike ride away. Longboat Key is a short drive or just grab the nearby free Bay Runner trolley that runs daily every twenty minutes 7am–11pm to St. Armands Circle, then to Lido Beach Park with its huge pool and amenities then on to unspoiled South Lido Beach with its nature walks, see the photos. Unit #107 checks off every box for worry-free elegant, but affordable, downtown living with easy beach access. With its own covered parking and only 12-minutes by Uber to the airport Unit #107 could be your elegant city pied-a-terre, investment property, or live full-time downtown and walk everywhere.
4662 BEACON DR, SARASOTA, FL 34232
$390,00028 Days on yellowkey MLS ID: A4686944
0 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1609 Built: 1977 Tax: $1,991 (2025)Community: Sarasota SpgsSingle Family
Taxes:$1,991
Elementary School: Brentwood Elementary
Remarks: Under contract-accepting backup offers. Check out this 3-bedroom, 2-bath home with a 2-car garage in a centrally located neighborhood. This home features a split floor plan with a spacious formal living room, a separate family room at the rear of the home, and a formal dining room with built-in buffet-style cabinets. The galley kitchen is conveniently located in the center of the home, and there is an abundance of closet space throughout. This property does need some TLC, but the major updates include a roof replaced in 2019, A/C in 2013, and water heater in 2016. The partially fenced backyard offers a large 16x30 wood deck built around a beautiful oak tree, plus a spacious 14x11 shed with two loft areas, ideal for extra storage, a workshop, a man cave, or a she shed, with a paver brick patio off it. Located within walking distance to the elementary school and a neighborhood park with grills and picnic tables, and just a short drive to shopping, restaurants, and the beautiful beaches. Don’t miss this great opportunity to make this home your own
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Lisa Bouck, Pa (941-374-0165)
941 VIRGINIA DR, SARASOTA, FL 34234
$1,500,00050 Days on yellowkey MLS ID: A4684540
Bed: 6 Bath: 4.5 Liv Area Sq Ft: 3492 Built: 1945 Tax: $9,217 (2025)Community: Bay HavenSpa: YesSingle Family
Taxes:$9,217
Elementary School: Emma E. Booker Elementary
Remarks: A Rare Piece of Sarasota History with current income of over 167,000 / yr. Four turn-key furnished residences. Three City Lots. One Extraordinary Piece of Sarasota History. Welcome to 941 Virginia Drive, a truly unique historic property originally built by John Ringling Jr., offering vintage Sarasota charm paired with modern flexibility and lucrative income. Set on three city lots, this 125-foot-long masonry residence creates an extraordinary private compound with four distinct living spaces. The main residence features two bedrooms, one and a half bathrooms, and an office or den, highlighted by timeless architectural details including stone porches, arched doorways, pecky cypress paneling, tall vaulted beamed ceilings and a wood-burning fireplace. Modern updates complement the historic character with stainless steel appliances, granite countertops, and updated fixtures. The property is designed for lifestyle, opportunity and flexibility for extended family, guests or continued successful short-term rental business. In addition to the main home, the estate includes three separate guest residences providing privacy and versatility. There are two in-law suites that feature full kitchens, a private pool, hot tub, outdoor shower, patio access and a private bathroom; one offers one bedroom and the other two bedrooms. There is an additional one-bedroom dwelling with a convenient kitchenette, private bathroom and laundry. Located just two miles north of downtown Sarasota, the property offers easy access to Lido Key, Longboat Key, St. Armands Circle, and the vibrant dining, arts, and cultural scene of downtown Sarasota. Whether you envision a private historic estate, a multi-generational compound or a unique established vacation rental business, this rare property offers exceptional character, privacy and opportunity in one of Sarasota’s most desirable locations. Don’t miss this opportunity to Own a Piece of Ringling History — A Private Sarasota Compound with Vintage Charm and Resort-Style Living.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Angela Adams (941-809-9760)
3409 SPANISH OAK TER, SARASOTA, FL 34237
$155,000169 Days on yellowkey MLS ID: A4670478
1 Days Off yellowkey (back on 4/13/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 749 Built: 1973Monthly Fee: $210 Tax: $1,728 (2024)Community: Oakwood ManorMobile Home
Taxes:$1,728
Remarks: OAKWOOD MANOR — WHERE FUN, FRIENDSHIP & EASY LIVING COME TOGETHER!!! Smart Buyers Know-Value lives at Oakwood Manor Updated Gem in Oakwood Manor! Enjoy resort-style living in this highly desirable 55+ resident-owned community located within Sarasota city limits. Spanning 90 beautifully maintained acres, Oakwood Manor offers an exceptional lifestyle with a low monthly fee of just $210. Community amenities include a welcoming clubhouse with commercial kitchen and event stage, fitness center, library, heated pool, spacious hot tub, bocce ball and shuffleboard courts. Pickleball enthusiasts will appreciate the brand-new courts along the Legacy Trail, just a short bike ride away. (Please note: no pets, motorcycles, or RVs permitted.) Pride of ownership is evident throughout this meticulously maintained and tastefully decorated 2-bedroom, 2-bath home. The enclosed Florida room adds valuable living space and features a light, beachy ambiance, while a second front Florida room—surrounded by newer windows—is the perfect place to enjoy your morning coffee. Inside, the inviting living room is ideal for relaxing or entertaining. The kitchen offers a charming breakfast area, built-in desk, ample cabinetry, and includes a smooth-top stove, microwave, and refrigerator. Both bathrooms have been beautifully updated, and the coastal color palette throughout perfectly complements the Florida lifestyle. Notable upgrades include: AC replaced in 2020 • Bathrooms updated in 2020 • New tile bath floor (2020) • New flooring throughout (2021) • New windows • PVC plumbing • New front awning (2024) • New washer & dryer (2024) This move-in-ready home needs absolutely nothing—just bring your suitcase and start enjoying life in paradise. Ideal as a winter retreat or full-time residence. Conveniently located near downtown Sarasota, Siesta Key Beach, St. Armand's Circle, shopping, Sarasota-Bradenton International Airport, and two major hospitals—this home offers the perfect blend of comfort, convenience, and community. Schedule your private showing today—this is a must-see home and you won’t be disappointed!
Listing is courtesy of: REAL ESTATE BOUTIQUE LLC (941-726-8061)
Listing Agent: Maria Atkins (941-726-8061)
1775 STAPLETON ST, SARASOTA, FL 34239
$1,545,000174 Days on yellowkey MLS ID: A4670359
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2853 Built: 2007Monthly Fee: $568 Tax: $8,620 (2024)Community: Granada ParkSingle Family
Taxes:$8,620
Remarks: Between North Siesta Key and Oyster Bay, this coastal craftsman contemporary residence offers the leisure of a maintenance-free lifestyle in a desirable location. Visit nearby shopping and dining, or just a quick drive to Siesta Key Beach or downtown Sarasota. Positioned across from the community pool, the home offers easy-care landscaping complemented by a charming herb garden. Built of solid concrete block construction for lasting durability, recent improvements include new UV purification in air-conditioning units, a new roof and fresh exterior paint. The well-designed floor plan offers four bedrooms and three baths, with a flowing open layout that connects the great room, dining area and kitchen beneath high ceilings filled with natural light. A private guest suite above the garage provides flexible space for multi-generational living, a studio or fitness retreat. Throughout the home, refined details like solid-wood cabinetry, deep-trimmed windows and fine millwork reflect craftsmanship and quality. The great room impresses with a two-story ceiling and fireplace, while the kitchen showcases shaker cabinetry, quartz countertops, a center island, stainless-steel appliances and a walk-in pantry. Living in Granada Park provides the ease of a lock-and-go lifestyle in a gated, established neighborhood. This pleasant haven is conveniently just .3 miles from Publix, .5 miles to CineBistro, 1.3 miles to Southside Village, two miles to Sarasota Memorial Hospital, 2.6 miles to downtown Sarasota and five miles to Siesta Key Beach. It’s the best of Sarasota living, wrapped in a maintenance-free, West of Trail lifestyle.
Listing Agent: Andrew Tanner (941-539-0998)
1022 S OSPREY AVE, SARASOTA, FL 34236
$1,599,000204 Days on yellowkey MLS ID: A4666624
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2284 Built: 1922 Tax: $4,185 (2024)Community: Rigbys SubSingle Family
Taxes:$4,185
Remarks: Situated in the highly desirable West of Trail neighborhood of Hudson Bayou, this fully restored 1922 residence is the perfect blend of historic charm and modern conveniences. The property offers 2,284 square feet with two bedrooms and two bathrooms in the main house, plus a one-bedroom, one-bathroom guest house. Renovations include a 2006 conversion of the garage into a guest house with a stucco privacy wall and Chicago brick driveway. In 2018, a spacious primary suite with double closets, a large bath, and French doors to a screened lanai was added. High ceilings, oversized impact windows, and refinished hardwood floors (2024) add to the home’s appeal. Recent updates include a recoated roof with a 10-year transferable warranty (2025), A/C (2023), water heater (2024), encapsulated crawlspace with dehumidifier (2024), foundation reinforcement with new support jacks (2024/2025), and hurricane-rated windows. The kitchen and dining area were fully renovated, featuring custom Conestoga cabinetry and designer appliances (2024/2025). Additional features include recessed lighting, custom closets, a Murphy bed, and a natural gas fireplace. A wellness room with an infrared sauna (2025) completes the interior. Exterior highlights include enhanced landscaping, three all-weather sheds, a pergola with natural gas grill hookups, and a serene brick courtyard surrounded by mature landscaping for privacy. The location is unparalleled, with proximity to Southside Village, the downtown Sarasota bayfront, St. Armands Circle, and the world-famous beaches of Lido and Siesta Key.
Listing Agent: Barbara May (404-822-9264)
2960 SANDRINGHAM PL, SARASOTA, FL 34235
$525,000131 Days on yellowkey MLS ID: TB8453203
REDUCED by $15,000 (2.8%) on 04/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2205 Built: 1991Monthly Fee: $700 Tax: $3,335 (2024)Community: Sandringham PlaceSingle Family
Taxes:$3,335
Remarks: Absolute stunner and an exceptional value. This fully remodeled (2025) 3-bedroom, 2-bath, 2-car garage home in The Meadows offers 2,205 sq. ft. of beautifully updated living space on just under a 1/3 of an acre (0.30-acre) lot. The property features an open, split-bedroom floor plan with 10-foot ceilings and a soaring cathedral ceiling in the great room. The brand-new kitchen includes stainless steel appliances, quartz countertops, new cabinetry, and updated lighting. Both bathrooms have been fully renovated with new tile, faucets, finishes, and fixtures. Additional upgrades include new laminate wood flooring throughout and fresh interior paint. The home offers a large living room with a fireplace, a formal dining room, and a spacious primary suite with an oversized walk-in closet, dual sinks, a large walk-in shower, and a stand-alone soaking tub. A 252 sq. ft. air-conditioned Florida room, a generous utility room with a sink, and an oversized garage provide added versatility and convenience. Enjoy a maintenance-free lifestyle with an HOA that covers landscaping, lawn care, irrigation, power washing, tree trimming, and exterior paint. The property is located in Flood Zone X, meaning flood insurance is not required—an excellent advantage for buyers. The Meadows is a highly sought-after, park-like community featuring extensive amenities, including social activities, miles of nature trails, three golf courses, 15 lighted tennis courts, pickleball and basketball courts, a new Lifestyle and Wellness Center, a Jr. Olympic pool and spa, and protected nature preserves. A professional, 24-hour vehicle-based security patrol provides added peace of mind. Ideally situated just minutes from the University Town Center Mall, boutique shopping and dining, Nathan Benderson Park, downtown Sarasota, and world-class Gulf beaches.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (813-259-0000)
Listing Agent: Lawrence Malloy (813-679-3990)
4341 NELSON AVE, SARASOTA, FL 34231
$415,00014 Days on yellowkey MLS ID: A4688886
0 Days Off yellowkey (back on 4/9/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1686 Built: 1998 Tax: $2,113 (2025)Community: Golf EstatesSingle Family
Taxes:$2,113
Remarks: Under contract-accepting backup offers. PROFESSIONAL PICTURES TO COME!! Welcome to 4341 Nelson Avenue—a well-loved single-family home full of charm, comfort, and thoughtful features. This inviting property offers generous closet space throughout, making organization easy and practical for everyday living. Enjoy peace of mind with a newer roof, adding value and durability to the home. The spacious primary bedroom provides direct access to a large lanai, creating the perfect private retreat to relax with your morning coffee or unwind in the evenings. Step outside to a beautifully landscaped yard filled with lush vegetation, offering a serene and natural setting. The partially fenced backyard provides both privacy and flexibility—ideal for pets, gardening, or outdoor entertaining. With its warm character, functional layout, and inviting outdoor spaces, this home is a wonderful opportunity to enjoy the best of Sarasota living.
Listing Agent: Daina Filiatreau (941-932-3414)
5531 ROSEHILL RD #203, SARASOTA, FL 34233
$179,900134 Days on yellowkey MLS ID: A4674707
REDUCED by $20,000 (10.0%) on 04/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1316 Built: 2002 Tax: $2,572 (2025)Community: Admirals WalkCondo
Taxes:$2,572
Remarks: Discover the perfect blend of style, comfort, and convenience in this refreshed 2-bedroom, 2-bath corner-unit condo in the gated community of Admirals Walk. Featuring a versatile loft space—ideal for a home office, guest room, playroom, or extra lounge—this layout offers the flexibility today’s lifestyle demands. Step inside to an open floor plan with vaulted ceilings and plenty of natural light. The kitchen, flows effortlessly into the spacious living and dining area—perfect for hosting friends, relaxing after work, or enjoying family time. Both bedrooms include walk-in closets and en-suite bathrooms, and the conveniently placed laundry room sits between them for easy everyday living. Located just 6 miles from Siesta Key Beach and minutes from Clark Road and I-75, this home puts you close to schools, hospitals, shopping, dining, and everything Sarasota has to offer. Admirals Walk is a pet-friendly, maintenance-free community featuring resort-style amenities: a beautiful clubhouse with a pool and jacuzzi, modern fitness center, game room, and meeting spaces. Your association fee even includes internet, cable, water, sewer, trash, and security, offering excellent value and peace of mind. This condo delivers the Florida lifestyle you’ve been searching for. Schedule your showing today!
Listing Agent: Brett Keyser, Jr (941-957-8425)
33 S PALM AVE #1601, SARASOTA, FL 34236
$3,950,000279 Days on yellowkey MLS ID: A4659041
2 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3407 Built: 2024Community: DemarcayCondo
Taxes:$0
Remarks: Under contract-accepting backup offers. Penthouse Collection residence on the 16th floor of the newly built DeMarcay, capturing commanding vistas over downtown Sarasota, Sarasota Bay, Big Pass and the Gulf. Perfectly positioned at the corner of Main Street and Palm Avenue, this address places art galleries, acclaimed dining, boutiques, theaters, the farmers’ market, the city marina, wellness studios and live music within an easy stroll. Plus, St. Armands Circle and Lido Beach are just three miles across the Ringling Bridge. DeMarcay sets a new benchmark for downtown living with elevated, resort-inspired amenities crowned by an 18th-floor bi-level terrace with 360-degree views. Residents enjoy a state-of-the-art fitness center, club lounge, outdoor kitchen, and a spectacular pool terrace designed for sunset lounging and entertaining, supported by dedicated on-site staff available 24/7 for personalized service. This is the only condominium in downtown Sarasota with 24/7 valet parking service, offering a distinctive, space-saving parking configuration and the ease of round-the-clock attended vehicle access. Bayside on the 16th floor, this elegant 3,407-square-foot residence offers three private bedroom suites, a separate office/den, powder room, open-concept living, laundry facilities, and a private bayfront balcony. Volume ceilings and expansive glass invite natural light and frame the skyline and water views throughout. The gourmet kitchen features imported Italian cabinetry, quartz countertops, a Miele five-burner gas cooktop, and integrated Miele appliances. The primary suite is a true retreat with a spa-inspired bath showcasing designer Italian cabinetry, porcelain undermount sinks, a soaking tub and a spacious walk-in shower. An 18-story boutique condominium of only 39 residences, DeMarcay uniquely weaves modern architecture with Sarasota history, thoughtfully preserving and restoring the iconic facades of the original DeMarcay Hotel (1922) and the Roth Cigar Factory (1923–1938). A rare opportunity to live above it all: At the city’s most walkable crossroads surrounded by water, culture and coastal ease.
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