Location: Sarasota
Keyword(s): Booker Middle
Keyword(s) Middle School: Booker Middle
Do Not Show Listings
1750 BENJAMIN FRANKLIN DR #10G, SARASOTA, FL 34236
$1,175,000117 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,085
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Booker Middle
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)
3416 W CHELMSFORD CT #2, SARASOTA, FL 34235
$420,000507 Days on yellowkey MLS ID: A4634668
3 Days Off yellowkey (back on 5/26/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1513 Built: 1990 Tax: $4,165 (2023)Community: The MeadowsVilla
Taxes:$4,165
Elementary School: Gocio Elementary
High School: Booker High
Tax Year: 2023
Remarks: This beautiful villa sits at the end of a dead-end street, a few steps from the community pool and has stunning lake and golf course views. As you enter the walkway you are greeted by a gated entry gaining access to the front loggia that is accented with pavers and leads to your private entrance. The grand foyer is large and is the perfect space to display your art or family heirlooms. The kitchen has been professionally updated with stunning finishes and features high-end appliances. There is an office or den off the kitchen through dual pocket tiffany doors. The guest bedroom is spacious and provides a view to the front lanai. The living room and dining room provide for gracious living and entertaining allowing expansive views of the golf course and lake. Golf views are also from the primary suite with its large bathroom and walk-in closet. This home features high ceilings throughout, extensive levels of crown moldings, elegant features and finishes and is perfect for year-round living or as a wonderful getaway home for seasonal or frequent visitors.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: David Dangelo (941-587-7268)
800 N TAMIAMI TRL #815, SARASOTA, FL 34236
$975,000138 Days on yellowkey MLS ID: A4676300
REDUCED by $50,000 (4.9%) on 05/15/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1323 Built: 2007Monthly Fee: $1,328 Tax: $10,115 (2025)Community: AlinariSpa: YesCondo
Taxes:$10,115
Elementary School: Alta Vista Elementary
Remarks: Immerse yourself in the vibrant energy of Sarasota’s coveted Rosemary District, where an inspired coastal lifestyle unfolds just beyond your doorstep. Perfectly positioned, moments from The Bay Sarasota and The Quay Sarasota, this residence offers effortless access to the city’s most exciting transformation – lush bayfront greenspaces, scenic walking paths, a new pier, and curated waterfront experiences including free concerts, yoga, and even a kayak launch. Right at your doorstep you will discover a dynamic collection of Rosemary District café’s, acclaimed restaurants, artisan bakeries, and boutique shops, all contributing to a walkable, cultured, and endlessly engaging lifestyle. From morning rituals to sunset dinners along the bay, this residence, set within Alinari at Rosemary Place, invites you to experience Sarasota at its finest. Framed by breathtaking true full water frontage views that stretch across Sarasota Bay and beyond, this beautifully redesigned two-bedroom, two-bath residence captures unobstructed westerly vistas from its highly desirable eighth-floor position in the south tower, where natural light pours in and sunset gazing becomes a daily ritual. The interiors have been thoughtfully re-imagined with a clean, modern aesthetic, featuring wide plank luxury flooring, quartz surfaces, new modern fixtures, and a cohesive move-in ready design. The open layout enhances the connection to the water, while a rare walk-in laundry room and additional flex storage space add everyday convenience. The primary suite offers a serene retreat with a walk-in closet and a well-appointed, fully customized en-suite bath, while the second bedroom is equally versatile for guests or a home office – each space sharing in the residence’s captivating views. Alinari presents a refined residential experience with amenities beyond expectation. Enjoy the privacy of a 3rd floor Olympic length pool and deck where recreation and relaxation can easily be found. The state-of-the art fitness center, modern and fully upgraded theater, business center, guest suites, game room, gated entry garage, 24-hour concierge and on-site security, are just a small sample of Alinari features and lifestyle. Unique to the property you will enjoy a beautifully landscaped 35,000 sq ft gated recreational space that is for the exclusive enjoyment of Alinari owners and their pets. With strong reserves, no current assessments, and elevated construction in Flood Zone X, the building offers peace of mind and enduring value. Complete with two garage parking spaces and climate-controlled storage, this residence is a rare opportunity to enjoy downtown Sarasota living at the intersection of culture, convenience, and sweeping waterfront beauty.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Moriah Taliaferro (941-504-9910)
5021 BARRINGTON CIR #302, SARASOTA, FL 34234
$160,000228 Days on yellowkey MLS ID: A4663516
REDUCED by $15,000 (8.6%) on 05/26/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1078 Built: 1982Monthly Fee: $599 Tax: $2,471 (2024)Community: Barrington WoodsVilla
Taxes:$2,471
Elementary School: Emma E. Booker Elementary
Tax Year: 2024
Remarks: One or more photo(s) has been virtually staged. Embrace the ultimate Sarasota lifestyle in this beautifully maintained 2-bedroom, 2-bathroom villa, perfectly situated in a secure fenced community and featuring elegant, vaulted ceilings and two private screened lanais for enjoying the beautiful Florida weather. This property offers a low-maintenance, resort-style experience with a fantastic community pool and a dedicated carport for convenient parking. The villa's outstanding location provides quick access to both necessities and leisure: it's just minutes from Sarasota-Bradenton International Airport (SRQ), a short drive to the famous Gulf beaches, and centrally located near esteemed institutions like New College and the Ringling School of Art and Design. It's an ideal retreat for anyone seeking the perfect blend of security, comfort, and immediate proximity to Downtown Sarasota's rich scene of arts and culture.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER (941-729-7400)
Listing Agent: Kelly Oatsvall (941-447-7256)
1173 MYRTLE ST, SARASOTA, FL 34234
$375,000234 Days on yellowkey MLS ID: TB8436061
1 Days Off yellowkey (back on 5/26/2026)
REDUCED by $14,900 (3.8%) on 05/19/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1361 Built: 1950 Tax: $4,523 (2024)Community: Ford SubSingle Family
Taxes:$4,523
Remarks: Under contract-accepting backup offers. **SHORT TERM RENTALS PERMITTED** This beautiful property is conveniently located within the city limits of Sarasota, allowing for short-term rentals with a minimum of 7 days—offering a lucrative opportunity for investors. This updated home highlights a 3-bedroom, 2-bath layout featuring a separate primary suite complete with a luxurious new bathroom and kitchenette, providing the perfect setup if this space is used as a separate 1-bedroom, 1-bath studio—ideal for high-demand rentals in the area. Option #2 offers an incredible family retreat with plenty of privacy and a resort getaway feel right at home. With its own separate entrance, this flexible space also doubles as a fantastic in-law suite. Together, the spaces provide 1,361 square feet of refreshed living area. Step inside to discover new flooring throughout, a modern kitchen and updated bath, and stylish new lighting that enhances the home’s bright, open feel—all beautifully upgraded with new appliances, AC, water heater, and roof for lasting comfort and value. This property also boasts a generous yard—perfect for those who crave extra outdoor space. Whether you envision a private garden, play area, or space for family pets, this oversized side yard offers endless possibilities. Mature landscaping provides both beauty and privacy, creating a peaceful setting for outdoor relaxation. The outdoor area is made for Florida living—featuring an expansive, oversized pool perfect for lap swimming, entertaining, and making lasting memories. A huge screened lanai invites relaxation and provides plenty of space to host poolside gatherings and parties. A mini golf green adds a playful touch for family and friends. Whether you’re looking for a home with extra income potential or a flexible multi-use property, this one checks all the boxes. Conveniently located near downtown Sarasota, St. Armands Circle, Siesta Key Beach, the Sarasota-Bradenton Airport, and the UTC shopping district, you’ll be right in the heart of everything the Gulf Coast has to offer. A rare opportunity to enjoy a move-in-ready home and an income-producing asset—all in one desirable Sarasota location! **Free 1/0 Interest Rate Buy Down available when using our preferred lender.**
Listing is courtesy of: LPT REALTY LLC (813-359-8990)
Listing Agent: Andrew Duncan (813-359-8990)
5246 MANORWOOD DR #4C, SARASOTA, FL 34235
$350,00054 Days on yellowkey MLS ID: A4688263
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1997 Built: 2007Monthly Fee: $1,285 Tax: $3,889 (2025)Community: Grande Oaks PreserveCondo
Taxes:$3,889
Remarks: BEAUTIFULLY FURNISHED SPACIOUS PENTHOUSE living minutes from University Town Center-Gated resort amenities and almost NO maintenance responsibilities. Truly lock and leave. Experience elevated living in this exquisite penthouse residence sitting high amongst the Oak trees, ideally situated within the highly sought-after Grande Oaks Preserve, just moments from the vibrant University Town Center. This is a rare opportunity to own the only penthouse currently available in this exclusive, gated enclave, where solid block construction ensures both enduring quality and peace of mind. Upon entering, you are welcomed into a beautifully appointed three-bedroom, two-bathroom home defined by soaring 12-foot ceilings, elegant tray ceilings in both the kitchen and primary suite, intricate crown molding, and stately 8-foot doors that enhance the home’s light-filled, refined ambiance. The thoughtfully designed third bedroom offers versatility as a private study or guest retreat. Expansive French doors lead to a generously sized, screened lanai featuring impact-rated sliders and serene fountain views, creating an ideal setting for both quiet relaxation and effortless entertaining. The chef’s kitchen and spa-inspired baths showcase rich solid wood cabinetry, blending timeless craftsmanship with sophisticated style. Additional highlights include two spacious assigned indoor garage parking spaces and an oversized climate-controlled storage unit, providing both convenience and comfort. Residents of Grande Oaks Preserve enjoy an exceptional lifestyle INCLUDING access to resort-style amenities, including a sparkling pool and 2 spas, a fully equipped fitness center, clay tennis courts and pickleball courts, and beautifully maintained grounds within a secure, gated environment as well as water/sewer & trash removal. Perfectly positioned in one of Sarasota’s most desirable corridors, Grande Oaks Preserve offers an exceptional location that seamlessly blends convenience with an upscale, tranquil setting. Just moments away, University Town Center presents a premier destination for luxury shopping, fine dining, and entertainment, featuring renowned retailers and an array of top-tier restaurants. Residents enjoy effortless access to everyday conveniences, from boutique grocers to cafes and wellness services, all within a short distance. The community is also ideally situated near Nathan Benderson Park, a picturesque waterfront destination known for its walking trails, rowing events, and outdoor activities. A short drive brings you to the cultural and coastal treasures that define Sarasota living, including the pristine shores of Siesta Key Beach, consistently ranked among the finest beaches in the country. Downtown Sarasota, with its vibrant arts scene, theaters, galleries, and marina, is also easily accessible, offering an unmatched blend of sophistication and leisure. With convenient proximity to major roadways and just 12 minutes from Sarasota-Bradenton International Airport, travel is effortless, whether for business or pleasure. This extraordinary location places the very best of the region—shopping, dining, recreation, and world-class beaches—right at your doorstep while preserving the privacy and serenity of an exclusive gated community. This extraordinary penthouse offers a seamless blend of luxury, location, and lifestyle—an exceptional offering not to be missed. Schedule your private showing today.
Listing Agent: Tami Cashi (941-527-9088)
5450 LONGWOOD RUN BLVD #202, SARASOTA, FL 34243
$185,00080 Days on yellowkey MLS ID: A4685859
INCREASED by $5,000 (2.8%) on 05/20/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 954 Built: 1994Monthly Fee: $434 Tax: $2,087 (2025)Community: Magnolia PlaceCondo
Taxes:$2,087
Remarks: Locatin, location, location! Come see this spacious condo located in the heart of Sarasota. You are just 2.5 miles from University Town Center, I-75, shopping and dining. Sarasota Bradenton International Airport, downtown Sarasota, and beautiful Sarasota Bay are within 15 minutes. Longwood Park is only 0.4 miles away and here where you can enjoy dog-friendly areas, tennis and pickleball courts, basketball courts, baseball fields, a playground, gymnasium, a recreational building and more. This well-maintained condo offers two bedrooms and two bathrooms. An inviting open floor plan features a spacious great room, kitchen and dining area. Beautiful, engineered wood floors cover the entire condo. No carpet in this property! New water heater was installed in February 2026. You can enjoy scenic view from the covered and screened lanai. The community only has 16 condos. HOA fees cover your water/sewer, cable TV, interior/exterior pest control, exterior power washing/maintenance, irrigation/landscaping maintenance, as well as common area taxes and insurance.
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Delia Valente (571-236-7245)
2554 RUFFING CT, SARASOTA, FL 34237
$749,00071 Days on yellowkey MLS ID: A4686547
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2116 Built: 2022Monthly Fee: $654 Tax: $8,822 (2025)Community: Payne Park Village Phase 2Townhouse
Taxes:$8,822
Remarks: Under contract-accepting backup offers. Thoughtfully upgraded and impeccably maintained, this three-level townhome offers a refined take on low-maintenance living in a central Sarasota location, blending modern design with high-end finishes and everyday functionality. Featuring three bedrooms—each with its own private bath—plus an additional powder room, the layout is designed to provide both privacy and flexibility. An in-home residential elevator, installed at construction, connects all levels, enhancing convenience and long-term livability. The open-concept main living level serves as the heart of the home, where kitchen, dining, and living spaces flow seamlessly together. The kitchen has been extensively upgraded with Level 5 Calacatta Alta quartz countertops, cabinetry extended to the ceiling, a designer-wrapped island with added storage, and a Café appliance package with Bosch induction cooktop. A full-height tile backsplash, Hansgrohe professional faucet, and custom pantry shelving further elevate both form and function, while Rev-A-Shelf storage systems maximize efficiency. Upstairs, the primary suite offers a comfortable and well-appointed retreat with a tray ceiling and a custom-designed closet system featuring integrated lighting. The en-suite bath showcases upgraded fixtures and finishes, while all bathrooms throughout the home reflect a cohesive level of quality, including quartz countertops and designer upgrades. Throughout the home, attention to detail is evident in the Mohawk waterproof luxury vinyl plank flooring, upgraded lighting with dimmers, premium Sherwin-Williams paint, and enhanced hardware selections. Additional highlights include plantation shutters, custom Graber window treatments, hurricane-rated windows, and a full ADT security system with exterior cameras. The garage is equally well-equipped, featuring a custom storage system, overhead racks, additional lighting, and a secondary refrigerator, offering practical solutions for organization and storage. Beyond the home, the community offers a heated resort-style pool, private dog park, and professionally maintained landscaping, with association-provided insurance contributing to a simplified ownership experience. Ideally positioned near Payne Park—with tennis courts, walking trails, and green space—and providing direct access to the Legacy Trail, the location also offers walkability to downtown Sarasota’s dining, shopping, and cultural amenities, along with a nearby trolley stop for convenient access to the beaches. A well-executed combination of thoughtful upgrades, modern convenience, and a prime Sarasota setting—this residence delivers both comfort and quality in a highly accessible location.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Nikki Taylor (941-587-9060)
1659 DEVONSHIRE LN, SARASOTA, FL 34236
$2,495,000180 Days on yellowkey MLS ID: A4673505
REDUCED by $100,000 (3.9%) on 05/14/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2754 Built: 2024 Tax: $23,612 (2024)Community: Burns Realty Co SubSpa: NoSingle Family
Taxes:$23,612
Remarks: One or more photo(s) has been virtually staged. Welcome to Downtown Sarasota luxury living at its finest. Perfectly positioned in the sought-after Laurel Park neighborhood, just steps from Historic Burns Court, Marie Selby Botanical Gardens, Bayfront Park, Marina Jack, and only minutes to Lido Beach and St. Armands Circle, this custom-built 2024 coastal modern residence offers an exceptional blend of sophistication, comfort, and walkable downtown convenience. Designed for those who value effortless entertaining and an active Sarasota lifestyle, this meticulously constructed two-story residence spans 2,754 square feet and features four bedrooms, three and a half baths, a heated saltwater pool, outdoor kitchen, and thoughtfully curated designer finishes throughout. The heart of the home showcases an expansive open-concept living space centered around a chef's kitchen appointed with premium Thermador stainless appliances, gas cooking, built-in coffee and beverage center, oversized island seating for seven, walk-in pantry, dedicated ice maker, dual wine refrigeration accommodating over 200 bottles, and seamless indoor-outdoor flow ideal for entertaining. Step outside into a private resort-inspired setting where textured stucco privacy walls frame a heated saltwater pool with waterfall feature, fountains, ambient lighting, covered entertaining spaces, outdoor kitchen, pool bath, and outdoor shower. Constructed entirely of concrete block and engineered for peace of mind with CAT 5 hurricane windows, metal roof construction, whole-house Generac generator, water filtration systems, and exceptional finish quality throughout. The second level owner's retreat creates a private sanctuary with spacious walk-in closet and spa-inspired bath, while two guest suites share a beautifully appointed Jack-and-Jill bath. A first-floor bedroom with adjacent full bath offers flexibility for guests, office, fitness, or multigenerational living. Additional features include marble exterior decking, porcelain tile balconies, epoxy garage flooring, irrigation system, quartz surfaces throughout, and premium construction rarely found in downtown Sarasota. Leave the car behind and experience Sarasota the way it was meant to be lived — morning walks to Selby Gardens, evenings in Burns Court, waterfront sunsets along Bayfront Park, and effortless access to world-renowned beaches. Luxury. Lifestyle. Location. 1659 Devonshire Lane delivers all three. Some photos have been virtually staged. All measurements are approximate and should not be relied upon as exact.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Julie Kell (330-309-7022)
4345 CALLISTA LN, SARASOTA, FL 34243
$425,00051 Days on yellowkey MLS ID: A4688590
0 Days Off yellowkey (back on 5/1/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1930 Built: 2005Monthly Fee: $243 Tax: $4,396 (2025)Community: Callista VillageSingle Family
Taxes:$4,396
Remarks: Under contract-accepting backup offers. This light and bright home offers an inviting open-concept design with a spacious kitchen that flows seamlessly into the great room, creating the perfect setting for both everyday living and entertaining. Featuring 2 bedrooms, 2 bathrooms, a dedicated office/den, and a 2-car attached garage with a new epoxy finish, this home combines comfort, functionality, and style. The kitchen is equipped with newer stainless steel appliances, while the spacious owner’s suite provides a relaxing retreat with an oversized walk-in closet. Step outside and enjoy your own private saltwater swimming pool, offering a luxurious touch and silky-smooth water for year-round enjoyment. Additional updates include a new air conditioning system installed in 2021, annual servicing, UV lights, and a surge protector for added peace of mind. Pool pump replaced in 2023 and new salt cell and motherboard in 2025. Low community fees add to the appeal and cover yard and shrub maintenance, sprinklers and soakers, and front entrance maintenance. Located just beyond Longwood Park, residents also enjoy easy access to an impressive variety of nearby recreational amenities including baseball, basketball, pickleball, tennis, a playground, picnic pavilion, recreation building, gymnasium, and dog-friendly areas. All within walking distance! Welcome to Callista Village, an intimate community of just 32 homes ideally located west of UTC Mall, where exceptional shopping, dining, and everyday conveniences are all close at hand. A local bus stop just outside the community offers easy access to shopping, the airport, and downtown, adding even more convenience to this desirable location.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Brenda Wilson (941-321-8686)
5378 SARAPOINTE CT, SARASOTA, FL 34232
$550,00011 Days on yellowkey MLS ID: A4694119
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1988 Built: 1986Monthly Fee: $62 Tax: $3,186 (2025)Community: Eastpointe Ph 01Spa: NoSingle Family
Taxes:$3,186
Remarks: Under contract-accepting backup offers. Waterfront Pool Home. Tucked away on a quiet cul-de-sac in the sought-after Eastpointe community, this beautifully maintained 4-bedroom, 2-bath residence offers the perfect blend of comfort, privacy, and Florida lifestyle. Set on a scenic lakefront lot with tranquil water views, this home features a versatile floor plan with two primary suites, including a private second-floor retreat with its own mini-split system. Step inside to soaring vaulted ceilings in the living room, a cozy wood-burning fireplace, and a wet bar—ideal for entertaining. The eat-in kitchen is thoughtfully designed with convenient pull-out shelving in the cabinets, while many major appliances are less than one year old, adding peace of mind for the next owner. The outdoor living space is a true retreat, featuring a heated pool, expansive pavered pool deck, and an outdoor shower, all overlooking the peaceful lake setting. The spacious yard includes multiple fruit trees, creating your own tropical oasis. Additional upgrades include: Impact windows (2025) / Impact-rated garage door /Hardie fiber cement plank siding /Engineered acacia hardwood flooring in bedrooms/Solid core interior doors /Roof replaced in 2016 /A/C replaced in 2017 Located just minutes from downtown Sarasota, this home offers exceptional convenience—only 7.3 miles to Siesta Key Beach, close to Nathan Benderson Park, and near The Mall at University Town Center for premier shopping, dining, and entertainment. Easy access to I-75 makes commuting a breeze. With low HOA fees and no CDD, this exceptional waterfront home offers the ideal combination of location, upgrades, and lifestyle.
Listing is courtesy of: ALBERT WOOSTER & COMPANY (941-350-1220)
Listing Agent: Timothy Trojanowski (941-320-1399)
941 VIRGINIA DR, SARASOTA, FL 34234
$1,500,00088 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
Remarks: A Rare Piece of Sarasota History. 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)
800 BENJAMIN FRANKLIN DR #607, SARASOTA, FL 34236
$950,000221 Days on yellowkey MLS ID: A4669063
REDUCED by $50,000 (5.0%) on 05/11/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1150 Built: 1978 Tax: $11,434 (2024)Community: Lido AmbassadorSpa: NoCondo
Taxes:$11,434
Remarks: Experience the best of beachfront living at Lido Ambassador with this rarely available 6th-floor residence, lovingly maintained by long-time owners and offering captivating Gulf views, impact-rated windows and sliders, and endless potential to personalize. Perfectly situated on the sandy shores of Lido Beach and just moments from world-famous St. Armands Circle, this condo offers the ideal balance of coastal tranquility and vibrant Sarasota living. This two-bedroom, two-bath unit features a desirable split floor plan, open living/dining area, and a private balcony where you can soak in breathtaking sunset views, sea breezes, and the ever-changing colors of the coastline. Meticulously cared for over the years, this home is move-in ready or the perfect canvas to update to your personal style. The spacious primary suite offers ample closet space and an en-suite bath, while the guest bedroom and bath provide a private retreat for visitors. Natural light, a thoughtful layout, and the overall condition reflect the pride of ownership throughout. Lido Ambassador is a well-managed community of just 74 residences, known for its pristine grounds and attentive upkeep. The Gulf-front heated pool and sun deck are currently undergoing a full renovation, soon to reopen better than ever, with a refreshed, resort-style atmosphere for residents to enjoy. Additional amenities include a fitness center, catering kitchen, private storage, and assigned covered parking. Steps from the Lido Beach Resort Tiki Bar and short distance of St. Armands Circle, Longboat Key, and the arts and culture of downtown Sarasota, this location is unmatched. Whether you’re seeking a coastal getaway, investment opportunity, or full-time residence, this 6th-floor unit delivers exceptional location, views, and value. Discover why Lido Ambassador is one of the most coveted addresses on Lido Key.
Listing Agent: Lindsay Nock (941-735-7005)
5354 MYRTLE WOOD #50, SARASOTA, FL 34235
$247,000137 Days on yellowkey MLS ID: A4677059
REDUCED by $8,900 (3.5%) on 04/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1064 Built: 1981Monthly Fee: $592 Tax: $2,906 (2024)Community: SomersetSpa: NoVilla
Taxes:$2,906
Remarks: NEW PRICE- Welcome to a move-in-ready villa offering effortless Florida living in one of the most sought-after enclaves within The Meadows—where tree-lined streets, mature landscaping, and an active outdoor lifestyle define the experience. Perfectly positioned on a quiet street just moments from community pools and miles of scenic trails, this residence delivers both privacy and immediate access to everything that makes The Meadows so desirable. Inside, vaulted ceilings and an open, light-filled layout create an inviting sense of space, while recent updates—including fresh interior paint and new flooring—provide a clean, modern feel with minimal effort required. The great room seamlessly opens through a full wall of sliding glass doors to a screened lanai surrounded by lush greenery—an ideal setting for morning coffee or a relaxed evening. The kitchen offers a functional and stylish workspace with stone countertops, stainless steel appliances, ample storage, and its own access to a private front lanai. The split-bedroom floor plan enhances comfort and flexibility, with a private primary suite tucked at the rear of the home featuring dual closets and a walk-in shower. A second bedroom with an ensuite bath at the front provides an ideal space for guests or a home office. A dedicated laundry area adds to the home’s practical design. Living in The Meadows means enjoying a 1,650-acre park-like community with over 14 miles of trails, 85 lakes, and optional memberships to golf, tennis, pickleball, a junior Olympic pool, and a fitness center. Just minutes from Nathan Benderson Park, the vibrant shopping and dining at University Town Center, downtown Sarasota, and the renowned beaches of Siesta Key and Lido Key, this villa offers the ideal balance of convenience, lifestyle, and value—whether as a full-time residence or seasonal retreat. Make an appointment to see this villa today.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Andy Scherer (315-264-0944)
620 RAWLS AVE, SARASOTA, FL 34236
$1,440,00071 Days on yellowkey MLS ID: A4686636
REDUCED by $55,000 (3.7%) on 05/26/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2300 Built: 2017 Tax: $11,066 (2025)Community: Townhomes/Orange ClubSpa: NoTownhouse
Taxes:$11,066
Remarks: Welcome to luxury urban living in the heart of downtown Sarasota. Located in the highly sought-after Townhomes of Orange Club, this stunning three-story residence offers approximately 2,300 square feet of thoughtfully designed living space just steps from the charm and culture of Burns Court. This beautifully appointed townhome features three spacious bedrooms, each with its own private ensuite bathroom, providing comfort and privacy for both residents and guests. A private elevator services all levels, seamlessly blending convenience with sophistication. Designed for both everyday living and entertaining, the home is crowned by an expansive rooftop deck—your own private retreat in the city—perfect for sunset gatherings, outdoor dining, or simply enjoying the vibrant downtown skyline. With its premier location, modern design, and rare rooftop living, this residence embodies the very best of Sarasota’s downtown lifestyle.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Samantha Jennen (941-321-6095)
5723 DEER HOLLOW TRL, SARASOTA, FL 34232
$299,0005 Days on yellowkey MLS ID: TB8511154
Bed: 2 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 721 Built: 1985Monthly Fee: $45 Tax: $1,776 (2025)Community: Deer HollowVilla
Taxes:$1,776
Remarks: Location, location, location! Welcome to this 2 bedroom, 1 bathroom villa ideally situated in the heart of Sarasota with quick access to I-75, making commuting and exploring the area incredibly convenient. This move in ready home has already had the major updates completed for peace of mind, including a new roof in 2022 with a 10 year warranty, hurricane grade windows, slider, and front door installed in 2023, new AC in 2024, and replaced exterior siding. Enjoy low HOA fees of just $335 annually while taking advantage of community amenities including a playground and peaceful preserve walking paths. Whether you’re looking for a primary residence or a seasonal getaway this villa offers comfort, convenience, and value all in one. Perfectly positioned near the vibrant UTC area, this home is just minutes from Nathan Benderson Park, The Mall at University Town Center, top rated dining, shopping, Sarasota-Bradenton International Airport, Downtown Sarasota, and the world famous beaches of Siesta Key and Lido Key. Schedule your showing today!
Listing is courtesy of: PEOPLE'S TRUST REALTY (727-946-0904)
Listing Agent: Ali Kochno (813-766-7143)
630 CORWOOD DR, SARASOTA, FL 34234
$824,50041 Days on yellowkey MLS ID: A4690643
REDUCED by $50,500 (5.8%) on 05/25/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1897 Built: 1963 Tax: $7,711 (2025)Community: Corwood ParkSpa: NoSingle Family
Taxes:$7,711
Remarks: Discover the perfect blend of location, lifestyle, and future potential in this beautifully updated residence in the desirable Corwood Park neighborhood. Situated on an expansive ~0.22-acre lot, this property offers a rare opportunity to enjoy move-in-ready comfort today while preserving room for tomorrow’s vision. Thoughtfully renovated, the home showcases a modern kitchen with shaker cabinetry, new countertops, new High Efficiency washer and dryer and stainless-steel appliances, complemented by updated bathrooms, new tile flooring throughout, and impact patio doors. The outdoor space is equally impressive, featuring a refreshed pool area ideal for entertaining or relaxing under the Florida sun. What truly sets this property apart is the generous lot size, flexibility and expanded living spaces, demonstrating the strong upside potential for expansion or redevelopment. Surrounded by lush tropical vegetation and mature trees, the property offers privacy and a serene setting, with ample space to add square footage, a guest house, or enhanced outdoor living features—subject to local zoning. Ideally located west of the Trail, this home is just moments from Sarasota Bay, where you can enjoy evening sunsets, and only minutes to cultural landmarks like the Ringling Museum, Sarasota Jungle Gardens, downtown Sarasota, SRQ Airport, and world-class beaches. Whether you’re seeking a primary residence, seasonal retreat, or investment with upside potential, this property delivers location, land value, and lifestyle—all in one of Sarasota’s most promising growth corridors.
Listing is courtesy of: CCI REALTY (954-667-6692)
Listing Agent: Oscar Betancourt (954-854-3959)
3332 TALLYWOOD CT #7086, SARASOTA, FL 34237
$150,00023 Days on yellowkey MLS ID: A4692649
1 Days Off yellowkey (back on 5/25/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1109 Built: 1983 Tax: $975 (2025)Community: Tallywood Ph 1 & 2Condo
Taxes:$975
Elementary School: Tuttle Elementary
Remarks: Under contract-accepting backup offers. Welcome to easy Florida living in the desirable 55+ Tallywood community of Sarasota! This charming 2-bedroom, 2-bath condo offers a spacious and comfortable layout designed for relaxed living and entertaining. The home is clean, well maintained, and offers a great opportunity to personalize and update to your own taste and style. Enjoy a bright open living and dining area, a functional kitchen with ample cabinet space, and a private primary suite with en-suite bath and generous closet storage. The second bedroom and bath provide flexibility for guests, hobbies, or a home office. The second bedroom has a built in Murphy bed and built in desk, which both convey. Step outside to enjoy your private outdoor space and experience the lifestyle that makes Tallywood so special. This pet-friendly community offers wonderful amenities including a heated screened-in pool, shuffleboard courts, a dog park, and a welcoming community center where neighbors gather for social activities and events. Beautifully maintained grounds and a peaceful atmosphere create the perfect setting for active living. Conveniently located near shopping, dining, golf courses, medical facilities, and Sarasota’s world-famous Gulf Coast beaches, this villa is ideal as a seasonal retreat or full-time residence. Enjoy low-maintenance living in one of Sarasota’s most established and friendly 55+ communities.
Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)
Listing Agent: Jenifer Funk (941-330-3373)
1937 GOLD AVE, SARASOTA, FL 34235
$374,900103 Days on yellowkey MLS ID: N6142964
0 Days Off yellowkey (back on 4/24/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1723 Built: 1958 Tax: $3,079 (2025)Community: Kensington ParkSingle Family
Taxes:$3,079
Remarks: Under contract-accepting backup offers. ****BACK on MARKET. Buyer financing fell through**** Welcome to this charming 3-bedroom, 2-bath single-family home nestled in the established Kensington Park neighborhood of Sarasota. Offering over 1,700 square feet of living space, this home features a flexible and inviting layout with spacious living areas and a versatile bonus room—perfect for a home office, family room, or playroom. Situated on a generous lot, the property provides ample outdoor space and additional parking, including room for a boat, RV, or work trailer. The open floor plan is ideal for entertaining, while the split-bedroom design offers privacy and comfort. Newer roof, vaulted ceilings, solid wood cabinets, new stainless-steel appliances, and hurricane shutters add peace of mind, making the home truly move-in ready while still allowing room to personalize. This spacious home features a large fenced-in backyard made for relaxing or entertaining and an enclosed lanai perfect for your morning coffee or evening unwind, rain or shine. Conveniently located near shopping, dining, golf, parks, and world-renowned beaches, this home offers easy access to everything Sarasota has to offer. A perfect match for anyone seeking comfortable, flexible Florida living. Schedule your tour today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Vicky Imbriaco (941-586-7448)
5515 DOWNHAM MDWS, SARASOTA, FL 34235
$699,00095 Days on yellowkey MLS ID: A4681324
REDUCED by $26,000 (3.6%) on 05/21/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2640 Built: 1992Monthly Fee: $193 Tax: $4,691 (2025)Community: Devonshire PlaceSpa: YesSingle Family
Taxes:$4,691
Remarks: Curb appeal begins at the street with beautifully selected driveway pavers that create an inviting approach and set the stage for what awaits inside. Step through the double-door entry and you are immediately drawn to sweeping views—across the expansive lanai and solar-heated pool and spa, over the tranquil lake that winds through The Meadows, and onward to the lush fairways of the golf course. * * * Offering 3 bedrooms, 2.5 baths, and 2,640 square feet under air, this thoughtfully designed residence provides a comfortable and highly functional layout ideal for both everyday living and entertaining. The primary suite is privately situated apart from the secondary bedrooms, creating a peaceful retreat, while the guest bedrooms at the opposite end of the home offer flexibility and privacy for family or visitors. * * * Multiple living spaces enhance the home’s versatility, including formal living and dining rooms, as well as a spacious great-room style family room that includes a casual dining area just off the kitchen. A striking coral stone fireplace serves as a beautiful focal point in the family room, adding warmth, character, and architectural interest to the space. * * * The kitchen is light and bright, featuring white cabinetry and light gray countertops that create a fresh, timeless feel. Abundant, well-designed cabinetry surrounds the cook, offering exceptional storage and an efficient layout that makes meal preparation both comfortable and convenient. * * * Outdoor living is equally impressive. The large screened lanai, solar-heated pool, and spa provide the perfect backdrop for relaxing afternoons, evening swims, or entertaining friends while taking in picturesque water and golf course views. The seamless indoor-outdoor flow embodies the very best of the Florida lifestyle. * * * Residents of The Meadows enjoy one of Sarasota’s most established and amenity-rich communities, known for its scenic lakes, miles of walking and biking trails, golf and social opportunities, and convenient proximity to University Town Center, I-75, downtown Sarasota, and renowned Gulf Coast beaches. * * * A home that combines generous living spaces, exceptional views, and an outstanding location—an opportunity not to be missed.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Marilyn Kneafsey (941-373-0999)
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