Location: Sarasota , 34234
Do Not Show Listings
1040 SYLVAN DR, SARASOTA, FL 34234
$1,450,000119 Days on yellowkey MLS ID: A4687776
REDUCED by $45,000 (3.0%) on 07/17/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1949 Built: 1980 Tax: $15,027 (2025)Community: Sylvan ShoresSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$15,027
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: An exceptional opportunity awaits to create your dream waterfront retreat in one of Sarasota’s most desirable locations. This unique property offers the rare chance to either complete the existing structure to your exact specifications or design and build a custom home tailored to your vision. Set on a private, serene lot surrounded by lush greenery, the property provides a peaceful, tucked-away feel while still being remarkably close to everything Sarasota has to offer. Enjoy excellent boating water with direct access to Sarasota Bay and the Gulf, making it a true paradise for boating and water sport enthusiasts. The property is already equipped with a dock and boat lift, so you can start enjoying the waterfront lifestyle right away. Located on a quiet, tree-lined street, this homesite combines tranquility with convenience. You’ll be just minutes from Bayfront Park, downtown Sarasota’s vibrant shops and restaurants, the Ringling Museum, Sarasota-Bradenton International Airport, and the University Town Center. Whether you envision a modern coastal masterpiece or a timeless waterfront estate, this is a rare chance to bring your vision to life in an unbeatable location with outstanding boating access and exceptional privacy.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Jennifer Linehan (941-266-7555)
5010 BARRINGTON CIR #2001, SARASOTA, FL 34234
$188,00018 Days on yellowkey MLS ID: A4698806
1 Days Off yellowkey (back on 7/17/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1420 Built: 1982 Tax: $2,786 (2025)Community: Barrington WoodsSpa: NoVilla
Taxes:$2,786
Elementary School: Emma E. Booker Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Under contract-accepting backup offers. Virtually Staged. Prime museum-area location and exceptional value! Discover this spacious, maintenance-free villa just minutes from downtown Sarasota. Nestled in a peaceful, lushly landscaped community, residents enjoy a sparkling pool and cabana overlooking a serene lake an ideal setting for easy Florida living. Inside, the home feels light, bright, and welcoming, with abundant windows and an airy layout. The roomy kitchen offers plenty of workspace along with a charming breakfast nook. The generous primary suite features a walk-in closet and en-suite bath, providing comfort and privacy. Two additional bedrooms offer flexibility for guests, a home office, or hobbies. The private screened lanai is perfect for morning coffee, evening relaxation, or enjoying Sarasota's signature indoor-outdoor lifestyle. A separate laundry room and a secure outdoor storage closet add everyday convenience for beach gear, gardening tools, or bikes. All of this in an unbeatable location near the Ringling Museum, Asolo Theatre, Sarasota Ballet, Ringling College, New College, the Bayfront, SRQ Airport, downtown dining and shopping, cultural venues, and world-famous beaches.
Listing Agent: Nancie Kalin (941-928-8833)
5013 BAY SHORE RD, SARASOTA, FL 34234
$1,500,000124 Days on yellowkey MLS ID: A4685711
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2671 Built: 1951 Tax: $9,542 (2025)Community: Sapphire ShoresSingle Family
Taxes:$9,542
Remarks: Discover the timeless allure of Indian Beach Sapphire Shores, one of Sarasota’s most captivating neighborhoods where history and modern living intertwine seamlessly. Established in the 1920s, this enchanting enclave exudes old-world charm while offering the vibrant lifestyle of a contemporary coastal community. Positioned perfectly between the glistening waters of Sarasota Bay and the bustling energy of downtown Sarasota, this neighborhood is where tranquility meets cultural sophistication. It's no wonder that John and Mable Ringling chose to make this neighborhood their home. Here in Sapphire Shores, life effortlessly blends outdoor beauty with unmatched convenience. Just beyond your doorstep, the iconic John and Mable Ringling Museum invites you to explore world-class art, history, and the grandeur of John and Mable's iconic home, the Ca’ d’Zan mansion—a Mediterranean Revival masterpiece that embodies the area’s rich heritage. This property gives you the rare opportunity to bring the home back to its mid-century grandeur, or build anew, the home of your dreams, in the most iconic neighborhood in Sarasota. This property has been previewed by home builders and contractors, if you would like to speak with them regarding the home's possible potential. Imagine starting your day with a serene walk along the bayfront at Sapphire Shores Park or Indian Beach Bayfront Park, where panoramic water views and golden sunsets create a picture-perfect backdrop or grab a cup of coffee and take a stroll up to the Ringling Museum and gaze at their famed banyan trees. This home is a major rehab with great character and good bones set on a lush .39 acre lot, with plenty of room for a pool. Stroll along the picturesque, tree-canopied Bay Shore Road, where majestic live oaks, sprawling banyans, and stately royal palms provide dappled shade. Despite its proximity to bustling U.S. 41, the area feels like an oasis, inviting you to explore its eminently walkable streets. Indian Beach Sapphire Shores also boasts proximity to Sarasota's cultural gems, including theaters, galleries, and fine dining, while serene beaches like Lido Key and Longboat Key beckon just minutes away. Adding to the neighborhood’s vibrancy are renowned institutions like New College, USF Sarasota-Manatee, and the Ringling College of Art and Design, infusing the community with creativity and intellectual energy. More than just a place to live, Indian Beach/Sapphire Shores offers a lifestyle of elegance, inspiration, and connection. Whether you’re drawn by its historic character, its artistic pulse, or the sheer beauty of Sarasota Bay, you’ll find yourself immersed in a neighborhood that truly has it all. Welcome to a place where every day feels extraordinary.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Worth Fiers Iii (941-812-3380)
3125 MONICA PKWY, SARASOTA, FL 34234
$335,00018 Days on yellowkey MLS ID: A4699082
1 Days Off yellowkey (back on 7/16/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1392 Built: 1961 Tax: $3,061 (2025)Community: New Leisures LakesSingle Family
Taxes:$3,061
Remarks: Under contract-accepting backup offers. Welcome to this charming Sarasota single family home, ideally located just minutes from vibrant downtown. Offering 2 bedrooms, 1 full bathroom and a flexible den/office/laundry space this home provides versatile living to suit your needs. The open plan living space includes a spacious eat-in kitchen and an inviting family room featuring a fireplace, perfect for a cozy night in or entertaining family and friends. The roof is 2016 and most of the house has hurricane impact windows. Step outside to a beautifully landscaped, fenced backyard with mature trees, including mango trees. With a covered patio, tree house and ample space, it is ideal for fun and relaxation. This property has NO HOA or CDD and an abundance of parking for an RV or a boat. An attached in-law suite with private entrance is currently occupied by a tenant, providing an added living space with existing rental income potential. Conveniently located near shopping, dining, parks and Sarasota's beautiful beaches, this property offers a wonderful combination of versatility, comfort and outdoor living. The property also includes solar panels with assumable financing. Don't miss out on this must see property!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Aisling Herron (941-263-9861)
1220 34TH ST, SARASOTA, FL 34234
$275,00018 Days on yellowkey MLS ID: A4699378
0 Days Off yellowkey (back on 7/16/2026)
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 999 Built: 1994 Tax: $3,751 (2025)Community: North Riverside ParkSingle Family
Taxes:$3,751
Middle School: Brookside Middle
Remarks: Under contract-accepting backup offers. An investment opportunity is already in place here, with this property operating as a multi-unit income producer in one of Sarasota's most consistently rented corridors near Ringling College and New College. Private, lockable bedrooms paired with shared common spaces give investors a turnkey setup, complete with an established rental configuration, proven occupancy appeal, and the option to keep the co-living format running or transition to a traditional long-term rental or primary residence. Inside, the home shows nicely with modern flooring, refreshed finishes, and an open, light-filled living area well suited to shared living. The kitchen offers crisp white cabinetry, stainless steel appliances, and hardwearing surfaces built to handle tenant turnover with ease. Updated bathrooms and smart room separation allow multiple occupants to live comfortably and privately under one roof. Freshly pressure washed and boasting updated landscaping, the exterior makes a clean first impression, while a covered front porch, fully fenced backyard, mature shade trees, a gravel seating area, and plenty of open yard give tenants inviting shared outdoor zones without adding upkeep. The location does much of the heavy lifting, sitting just minutes from Ringling College of Art & Design, New College of Florida, and downtown Sarasota, with Gulf beaches an easy drive away. Steady demand from students, creative professionals, and seasonal renters positions this property as a compelling long-term hold with built-in flexibility. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Toni Zarghami (941-248-2147)
659 MALDIVES TRL, SARASOTA, FL 34234
$999,990152 Days on yellowkey MLS ID: A4683422
REDUCED by $96,508 (8.8%) on 07/16/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3227 Built: 2026Monthly Fee: $250 Tax: $4,792 (2025)Community: GracewaterSingle Family
Taxes:$4,792
Remarks: Under Construction. Under Construction with anticipated completion date of April 2026. (Pictures current as of 5/12/26) Experience elevated living in the Grand Bay Haven at Gracewater, one of Sarasota’s most exciting new resort-style communities, with a projected completion date of mid-to-late April 2026. This stunning two-story residence offers over 3,200 square feet of thoughtfully designed living space, featuring 4 bedrooms, 3.5 baths, a private study, and an expansive loft/bonus room that provides flexibility for a media space, playroom, or additional guest retreat. Designed for both everyday comfort and effortless entertaining, the open-concept great room flows seamlessly into a chef-inspired kitchen appointed with quartz countertops, natural gas appliances, impact-rated windows and sliders, 8-foot interior doors, and elevated coastal finishes that create a bright, sophisticated ambiance throughout. The spacious primary suite serves as a private sanctuary with a spa-like bath and generous proportions, while three additional bedrooms and two full baths are ideally situated upstairs around the versatile loft area. Step outside to your covered lanai and enjoy your own private inground pool, creating the perfect setting for relaxing afternoons, weekend gatherings, and year-round Florida outdoor living. Located within the gated Gracewater community, residents enjoy a true lifestyle experience with a resort-style zero-entry pool and cabanas, elegant clubhouse, state-of-the-art fitness center, pickleball courts, dedicated dog park, and an on-site lifestyle manager coordinating social events and activities. Just minutes from downtown Sarasota’s dining, arts, and entertainment scene, world-renowned Gulf beaches, SRQ Airport, and convenient access to I-75, this exceptional new construction opportunity blends luxury, comfort, and location—allowing you to secure your place now and move into your brand-new Grand Bay Haven just in time to enjoy spring 2026 in style. (Builder has chosen finishes for the kitchen and bathrooms but different selections can be made if buyer goes under contract prior to installation)
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Richard Tyson (941-999-1179)
2947 GILLESPIE AVE, SARASOTA, FL 34234
$214,00012 Days on yellowkey MLS ID: TB8520023
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 864 Built: 1960 Tax: $2,577 (2025)Community: Newtown HeightsSpa: NoSingle Family
Taxes:$2,577
Elementary School: Phillippi Shores Elementary
Middle School: McIntosh Middle
Remarks: Welcome to this charming three-bedroom, one-bath home offering 864 square feet of comfortable living space in the historic Newtown Heights area, just minutes from the heart of downtown Sarasota. This home offers several important updates for added peace of mind, including a 2023 roof, 2025 AC system, an updated electrical panel installed in 2016, and newer windows. Inside, you’ll find newly installed luxury vinyl plank flooring throughout the main living areas and bathroom, while the kitchen features granite countertops and plenty of potential to make the space your own. Outside, the property includes a raised storage shed in the backyard, providing additional space for tools, equipment, and storage, along with a separate exterior laundry area. Conveniently located approximately two miles from downtown Sarasota, this home offers easy access to shopping, dining, entertainment, area beaches, and I-75 for convenient travel throughout the region. Whether you’re looking for an affordable place to call home or a property with plenty of potential, this Sarasota home is ready for its next owner. Buyer to verify public records for square footage, permitting, and home details.
Listing Agent: Justin Ure (813-382-8484)
5019 STEVENS DR, SARASOTA, FL 34234
$635,000153 Days on yellowkey MLS ID: A4683765
1 Days Off yellowkey (back on 6/13/2026)
REDUCED by $5,000 (0.8%) on 06/11/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1592 Built: 1957 Tax: $5,172 (2025)Community: Sapphire HeightsSpa: NoSingle Family
Taxes:$5,172
Remarks: Under contract-accepting backup offers. Fully renovated mid-century gem in the charming and highly coveted Indian Beach Sapphire Shores neighborhood of Sarasota. This exceptional three-bedroom, two-bathroom home has been lovingly preserved and thoughtfully restored with a strong emphasis on period-appropriate mid-century design and timeless style. Original terrazzo floors sparkle throughout the main living areas, honoring the home’s architectural roots. The fully renovated kitchen features new high-end appliances and blends seamlessly with the home’s classic aesthetic. The former Florida room has been transformed into comfortable year-round living space with permanent climate control, with the design anchored by an authentic vintage 1960s Preway wood-burning cone fireplace — a true statement piece. High-end mid-century light fixtures are showcased throughout, including multiple authentic Herman Miller pieces. Major updates provide peace of mind, including a new roof (2023), brand-new HVAC system and ductwork (2024), and a new solid wood privacy fence (2024). All bedrooms offer sizable closets, and the large zero-scaped front yard ensures beauty with minimal maintenance. The expansive backyard is a private retreat, featuring a generous paver patio and ample space for a pool or future additions. A newly installed barrel sauna and cold plunge create a spa-like sanctuary along the side yard, with convenient access from the principal suite. The true highlight of the home is the architect-designed principal bedroom and bathroom suite, completed in 2025 — an incredibly rare feature for this neighborhood and era. Designed as a private oasis, the light-filled bedroom includes a picture window and charming window seat, thoughtfully separated from the two guest bedrooms on the opposite wing of the home. The spacious en-suite bathroom is professionally interior designed and features high-end fixtures, a large walk-in shower, a freestanding spa tub, double vanity, and a walk-in closet. An exterior door provides direct access to the outdoor spa area for seamless indoor-outdoor living. Ideally located, this home is within a short distance to multiple beautiful waterfront parks and the renowned The John and Mable Ringling Museum of Art. Just five minutes to downtown Sarasota and ten minutes to the pristine beaches of Lido Key, you’ll enjoy the very best of Sarasota’s natural beauty and vibrant cultural scene — all from the comfort of your exquisitely restored mid-century home in one of the city’s most beloved neighborhoods.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Agnes Cameron (941-388-3966)
5119 GLEN ECHO AVE, SARASOTA, FL 34234
$129,00013 Days on yellowkey MLS ID: A4699867
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 720 Built: 1972 Tax: $3,094 (2024)Community: Tri-Par EstatesSpa: YesMobile Home
Taxes:$3,094
Tax Year: 2024
Remarks: Don’t miss this great opportunity to own a beautifully updated 2-bedroom, 2-bath 720 sq ft furnished single-wide home—perfect as a comfortable full-time residence or an easy winter getaway. Designed with a desirable split floor plan, this home features a newer TPO roof, new luxury vinyl flooring, drywalled walls and ceilings with recessed lighting, and a completely remodeled kitchen with granite countertops and soft-close cabinets. The enclosed lanai, complete with a portable AC unit, adds extra space to relax and enjoy the Florida lifestyle in comfort. Whether you’re a retiree looking for low-maintenance living or a snowbird searching for the perfect seasonal retreat, this move-in-ready home offers comfort, convenience, and value. Tri-par Estates is a 55+ community that provides a wealth of amenities: enjoy a heated and cooled large pool for year-round swimming, a brand-new spa, tiki hut, pickleball courts, fitness center, shuffleboard, miniature golf, horseshoes, and various recreation hall rooms equipped with ping-pong, billiards, card tables, a kitchenette, sewing areas, and more. The expansive clubhouse regularly hosts dinners, dances, and other events. Situated only minutes from downtown Sarasota, you’ll have easy access to marinas, shopping, restaurants, museums, the world-renowned Siesta Key and Lido Key beaches, and Sarasota airport. In this special park and recreation district, residents own their land directly, with no separate HOA fees—an annual fee of $1,648 is included in your property taxes. Internet and TV included in the annual fee This is also a golf cart-friendly community with optional RV or boat storage when available. Don’t miss the opportunity to join this lively, well-established neighborhood in paradise.
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Angelo Sammarco (941-284-5673)
2228 25TH ST #2228/2232, SARASOTA, FL 34234
$419,90025 Days on yellowkey MLS ID: A4698569
REDUCED by $10,000 (2.3%) on 07/14/2026
Bed: 6 Bath: 0.0 Liv Area Sq Ft: 2132 Built: 1988 Tax: $5,270 (2025)Community: New HarlemSpa: NoApartment
Taxes:$5,270
High School: Sarasota High
Remarks: Investors with an eye for both stability and upside, take note: this fully occupied duplex delivers two distinct three-bedroom, one-and-a-half-bath residences under a single, income-producing roof. Each unit carries its own half bath cleverly tucked off the primary bedroom, with easy-care tile flowing throughout—a detail tenants adore and owners appreciate come maintenance time. The financials speak softly but persuasively. Both sides are leased to long-term residents, generating dependable monthly returns from day one, while a roster of meaningful upgrades quiets the usual investor anxieties: full re-piping completed in 2024, energy-conscious tankless water heaters, and a roof refreshed in 2017. Two detached storage sheds, each wired with electric, lend flexibility that savvy landlords rarely find. Currently served by well and septic, the property sits close to central utilities at the street, and an RMF-2 designation may even permit an accessory dwelling unit—an enticing avenue for amplified yield, subject to city verification. Location sweetens the proposition considerably. Lime Lake Park rests a short distance away, offering green respite within minutes. Booker High School anchors the neighborhood with educational appeal, while the Phuoc Loc Tho Oriental Supermarket adds delightful culinary character to weekly errands. Convenient bus access along North Lockwood Ridge Road keeps connectivity effortless for residents and prospective tenants alike. Rarely does a turnkey, dual-income asset arrive so thoughtfully maintained and so generously positioned. Schedule your private tour today and let the numbers, and the neighborhood, make the case.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Don Chamberlain (207-329-8889)
2228/2232 25TH ST, SARASOTA, FL 34234
$419,90034 Days on yellowkey MLS ID: A4696124
Bed: 6 Bath: 3.0 Liv Area Sq Ft: 2132 Built: 1988 Tax: $5,270 (2025)Community: New HarlemSpa: NoHalf Duplex
2515 49TH ST, SARASOTA, FL 34234
$1,165,00032 Days on yellowkey MLS ID: A4693948
REDUCED by $30,000 (2.5%) on 07/14/2026
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3103 Built: 1957 Tax: $5,211 (2026)Community: Desoto AcresSpa: NoSingle Family
Taxes:$5,211
Tax Year: 2026
Remarks: One of Sarasota’s most unique and sought-after acreage communities, DeSoto Acres combines country living with all the city conveniences! No HOA and No CDD makes this a unique choice for freedom. This stunning county estate is nestled on 2.24 acres of land that’s fully fenced and gated. This private estate features a beautifully updated main residence, a fully equipped guest house, sparkling pool, tranquil pond, fire pit gathering area, oversized workshop shed, and room to truly live the Florida lifestyle. The main home offers over 2,300 square feet of updated living space including a spacious living and dining area overlooking the pool, granite countertops throughout the home, custom cabinetry with pull-out shelving and built-in appliance storage. A convenient breakfast nook area with built-in seating and additional storage. Flexible office/den space that can serve as a fifth bedroom., and an outdoor private shower off of the primary suite which is also accessible to the pool. The guest house is perfect for guests, multigenerational living, rental income, or a private home office. The guest house is approximately 800-square-feet and includes a full kitchen, panty, spacious living room, large bedroom with walk in closet, and full bath. It also features a dedicated laundry room, screened lanai, and its own yard and garden areas. Step outside and enjoy your own private Sarasota retreat including a sparkling pool, scenic pond, fire pit overlooking the water, mature landscaping and a large shed with power. Half of the shed has been converted into a large chicken coop with room for 20+ chickens with its own run. This rare piece of paradise offers room for gardens, animals, RVs, boats, and is ready for your vision. Conveniently located near Sarasota's stunning beaches, SRQ airport, UTC and so much more! Additional Features include- • Fully fenced and gated 2.24 acres • Two separate gated entrances • 3-car side-entry garage • 2-car carport • Pull-through garage bay • Wind-rated garage doors • Two HVAC systems • Well with newer pump • Water softener, filtration, and aerator systems • Tankless water heaters • Workshop with dog wash station • X Flood Zone The neighborhood’s historic agricultural overlay allows horses, chickens, roosters, and many other farm animals while remaining just minutes from shopping, dining, medical facilities, downtown Sarasota, University Town Center, and Gulf Coast beaches. Rarely does a property offer this much land, flexibility, privacy, and value this close to everything Sarasota has to offer! Whether you’re seeking multigenerational living, a private retreat, space for a home-based business, hobby farm, or simply room to breathe, this property delivers opportunities that are increasingly difficult to find in Sarasota.
Listing is courtesy of: COASTAL REAL ESTATE FLORIDA LLC (802-363-8776)
Listing Agent: Eric Jarvis (802-363-8776)
377 S SHORE DR, SARASOTA, FL 34234
$2,390,000334 Days on yellowkey MLS ID: A4662448
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1943 Built: 1954Monthly Fee: $3 Tax: $21,819 (2025)Community: Indian Beach - Sapphire ShoresSpa: NoSingle Family
Taxes:$21,819
Remarks: Amazing opportunity to create your waterfront estate in Sapphire Shores, where history, culture, and growth meet. This 16,378 sq. ft. lot offers 87 feet of water frontage, a private dock, and direct access to Sarasota Bay. Positioned along a quiet shoreline, it overlooks an almost 900-foot-wide deep-water basin, providing both privacy and natural beauty. Sapphire Shores combines legacy estates, striking new builds, and proximity to cultural landmarks such as The Ringling Museum and Asolo Theatre. With the North Trails ongoing transformation, including new developments, zoning updates, Ringling Colleges expansion the neighborhood is emerging as a prime location for luxury residences. Whether for a custom estate or a speculative project, this is a rare chance to secure a large waterfront property in one of Sarasota's most dynamic luxury neighborhoods.
Listing Agent: Kim Ogilvie (941-951-6660)
3315 BAY SHORE RD, SARASOTA, FL 34234
$22,000,000237 Days on yellowkey MLS ID: A4673690
Bed: 5 Bath: 10.0 Gar: 4 Liv Area Sq Ft: 10871 Built: 1987 Tax: $89,363 (2024)Community: Indian Beach Map OfSingle Family
Taxes:$89,363
Remarks: Set on 2.4 gated acres with an impressive 240 feet of pristine waterfront, this rare Sarasota compound offers over 10,000 square feet of pure privacy, serenity, and elevated coastal living. Perfectly positioned in the heart of the city yet worlds away, this estate delivers unobstructed, panoramic views of Sarasota Bay from nearly every room. Designed for both grand entertaining and intimate living, the residence welcomes you with a double-height foyer, cascading natural light, and a sense of scale that is both dramatic and warm. Across sixteen thoughtfully curated rooms, floor-to-ceiling windows frame endless water vistas, bringing the outdoors in and creating an atmosphere of true waterfront elegance. The estate features five spacious bedrooms and nine beautifully appointed bathrooms, including a breathtaking owners’ suite, a private, calming retreat with sweeping bay views, a spa-inspired bath, and a luxe outdoor shower surrounded by lush privacy landscaping. For those who value lifestyle and amenities, this property offers it all: A private tennis court tucked away behind mature tropical landscaping A well-appointed guest house ideal for extended stays A dedicated pool house for effortless entertaining A four-car garage for collectors and hobbyists Expansive terraces and outdoor lounging areas that overlook Sarasota’s most dramatic sunsets
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Inbal August (917-957-8111)
5304 CHERRY HILL AVE, SARASOTA, FL 34234
$126,60014 Days on yellowkey MLS ID: A4699773
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 960 Built: 1969Monthly Fee: $137 Tax: $2,844 (2025)Community: Tri-Par EstatesSpa: YesMobile Home
Taxes:$2,844
Remarks: Priced right and full of potential, this 2-bedroom, 1.5-bath home offers a welcoming layout with room to make it your own. Recent exterior updates include a newer TPO roof, vinyl siding, gutters, and a partially updated carport—giving you a strong start for future improvements. Inside, the open-concept design offers generous great-room coverage and square footage, with just enough separation to create cozy, functional spaces. Bring your imagination and explore the possibilities: refresh the finishes, modernize the kitchen and baths, or design a comfortable retreat that fits your style. This is a great opportunity for someone looking for value, flexibility, and a home ready for a personal touch. Tri-par Estates is a 55+ community that provides a wealth of amenities: enjoy a heated and cooled large pool for year-round swimming, a brand-new spa, tiki hut, pickleball courts, fitness center, shuffleboard, miniature golf, horseshoes, and various recreation hall rooms equipped with ping-pong, billiards, card tables, a kitchenette, sewing areas, and more. The expansive clubhouse regularly hosts dinners, dances, and other events. Situated only minutes from downtown Sarasota, you’ll have easy access to marinas, shopping, restaurants, museums, the world-renowned Siesta Key and Lido Key beaches, and Sarasota airport. In this special park and recreation district, residents own their land directly, with no separate HOA fees—an annual fee of $1,648 is included in your property taxes. Internet and TV included in the annual fee This is also a golf cart-friendly community with optional RV or boat storage when available. Don’t miss the opportunity to join this lively, well-established neighborhood in paradise.
1703 N TAMIAMI TRL #306, SARASOTA, FL 34234
$444,00038 Days on yellowkey MLS ID: A4697607
Bed: 1 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 810 Built: 2022 Tax: $4,737 (2025)Community: The Strand Of SarasotaCondo
Taxes:$4,737
Elementary School: Gocio Elementary
Remarks: A MUST SEE, sold TURNKEY AND FURNISHED (tastefully) and PRICED TO SELL! Welcome to this captivating condominium in the waterfront community: The Strand of Sarasota, built in 2022. The seller's thoughtful decor is inspired by a famous artist (Salvador Dali) with many upgrades including stone counters in kitchen and baths, luxury vinyl flooring, backsplash in kitchen, designer light fixtures and fans, upgraded LG washer in dryer, high end furnishings including a split king adjustable bed with massage capability, thoughtful designer finishes and the property has been lovingly maintained. Nine foot ceilings, impact rated doors and windows. Approximately 1 mile to downtown Sarasota and conveniently located to The Bay, Sarasota's arts, theater, shopping, restaurants, boutiques, bay front entertaining, marina, St. Armand's Circle and Sarasota's famous pristine white powdery sand beaches. Take a stroll along The Strand's 47 boat docks and enjoy the colorful and peaceful sunsets along Whitaker Bayou. The view from your spacious private balcony overlooks the serene azure heated pool and spa. Amenities include a gated community, on site management, waterfront community, fitness center, a parking garage space, additional storage space, ample guest parking, EVCSs, gas grills, fire pit, dog friendly community with dog park, kayak launch/storage. Investors are welcome as there is 1 week minimum rentals/ 52 times per year. This could be your full time home, a vacation getaway or an investment property in an affordable conveniently located waterfront community just minutes to downtown Sarasota.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Lisa Sebastian (941-544-5413)
1825 INNISBROOK LN, SARASOTA, FL 34234
$295,000374 Days on yellowkey MLS ID: A4659294
2 Days Off yellowkey (back on 7/13/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1054 Built: 2023Monthly Fee: $132 Tax: $2,027 (2024)Community: Tri-Par EstatesManufactured Home
Taxes:$2,027
Remarks: NEW home in Tri-Par Estates, one of the best Mobile home parks in the area and only 7.5 miles from the world famous Lido beaches. You actually own the land that your home is on. This gorgeous modern home is located on one of the largest lots in the park and has 2 bed, 2 bath, ranch style home that is spacious, with tons of light, plenty of closet space, crown molding, upgraded 2 panel doors & fixtures and beautiful high end laminate floors throughout. There are double sliding doors that lead onto the huge covered porch where you can sit and relax with your favorite beverage. The living room has a new a ceiling fan and has a wall equipped for you to hang your flat screen tv. The kitchen comes with new stainless appliances, a vented microwave, an oversized island, custom walnut cabinets with modern hardware & matching walnut valance over the kitchen window, an upgraded deep sink and faucet/spray combo, and plenty of cabinet space. Both bathrooms are well lit with additional windows, tile shower & bath, the continued walnut vanities with the ensuite having a bonus linen closet and a supreme glass barn door on the shower. The primary bedroom features dueling closets and both bedrooms are also braced for a ceiling fan and currently have light fixtures. This home is beautiful inside and out with roof to ground siding. The whole home is Class 3 hurricane rated including the shingled roof. The shingles are rated up to 180 miles per hour. Tri-Par Estates is loaded with amenities like shuffle board, pickleball, a pool, fitness center, horseshoes, put put golf and so much more. You are sure to be entertained in this fun & inviting community. Bedroom Closet Type: Built In Closet (Primary Bedroom). A 1 yr pest extermination program is included and transferable to the buyer. No Water Intrusion from past storms.This home is move in ready. It is being sold turn key and includes all furnishings. Just bring your clothes and toothbrush.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-907-2000)
Listing Agent: Tryla Brown Larson (941-962-1122)
993 GARY ST #A & B, SARASOTA, FL 34234
$460,00066 Days on yellowkey MLS ID: A4694443
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1679 Built: 1958 Tax: $5,119 (2025)Community: Harriet SubApartment
Taxes:$5,119
Remarks: Lender incentive available for qualified borrowers on primary residents only. Exceptional income-producing duplex located within the Sarasota city limits in desirable Flood Zone X, meaning no flood insurance is required. This solid block construction property offers multiple investment opportunities including owner-occupancy, short-term rentals, long-term rentals, student housing, or a hybrid income strategy. Located directly across from the revitalized North Water Tower Park, residents and guests can enjoy paved walking trails, a disc golf course, playground, covered picnic areas, public restrooms, and a water bottle filling station. Each private unit features 2 bedrooms and 1 bathroom with beautifully updated kitchens showcasing shaker cabinetry, quartz countertops, timeless restored terrazzo flooring, open-concept living areas, private laundry rooms, screened lanais, and covered carports with locked storage. Unlike many duplexes, the units do not share a common wall or yard space, offering enhanced privacy and reduced noise between occupants. Major capital improvements have already been completed within the past seven years, including the roof, dual HVAC systems, and water heaters. Additional investor-friendly features include separate utilities and durable block construction. The property’s central location provides quick access to Downtown Sarasota, Bradenton, Lakewood Ranch, SRQ Airport, Ringling College, New College, University of South Florida, and world-famous Gulf beaches, supporting a strong tenant and guest pipeline with future rental growth potential. According to the City of Sarasota permitting website, the occupancy use is listed as R1 Hotels/Motels/Boarding House, creating flexibility for multiple income-producing uses. Unit B has been operating as a short-term rental through Airbnb and VRBO since January 2026 and has already generated approximately $13,926 in rental revenue. Unit A is currently owner-occupied. The current owners originally purchased the property using FHA financing as their primary residence, demonstrating an excellent opportunity for buyers interested in “house hacking” by living in one unit while offsetting expenses with rental income from the other. With three major colleges nearby, the property also presents excellent potential for student housing demand. Whether you are an investor seeking cash flow, a buyer looking to offset monthly expenses through owner-occupancy, or someone searching for a flexible income-producing property in a rapidly growing Sarasota location, this duplex offers outstanding versatility and long-term upside potential.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Marius Mocan (503-858-3756)
776 ANEGADA LN, SARASOTA, FL 34234
$729,99045 Days on yellowkey MLS ID: A4696936
REDUCED by $64,180 (8.1%) on 07/11/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2201 Built: 2025Monthly Fee: $250 Tax: $4,506 (2025)Community: Gracewater At SarasotaSpa: YesSingle Family
Taxes:$4,506
Remarks: Pool home in the sought after Gracewater Community right in the heart of Sarasota. Our Waters Edge home offers generous living space for the whole family to enjoy. With 4 bedrooms, 2.5 bathrooms there’s plenty of room for everyone to have their own space. And when it’s time to come together, the open kitchen and great room provide the perfect setting for gathering and entertaining. The attached two-car garage offers convenience and peace of mind for storing vehicles and equipment. The lanai and pool area add even more excitement to this already impressive home. Gracewater is a maintenance free, gated community minutes to downtown and beaches.
Listing is courtesy of: PRIVADA REALTY (941-233-6000)
Listing Agent: Perry Pope (941-737-9124)
2480 ALAMEDA AVE, SARASOTA, FL 34234
$1,395,00054 Days on yellowkey MLS ID: A4695803
REDUCED by $55,000 (3.8%) on 07/01/2026
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2421 Built: 1960 Tax: $8,192 (2025)Community: Sarasota Bay ParkSpa: NoSingle Family
Taxes:$8,192
Remarks: Located within Sarasota city limits in the Indian Beach/Sapphire Shores neighborhood, 2480 Alameda Ave offers a beautifully remodeled, move-in ready home with real flexibility for how you use it. This 4-bedroom, 3.5-bathroom home was completely remodeled starting in 2021 with all-new plumbing, updated HVAC, new flooring, a reimagined kitchen, and fully remodeled bathrooms. The open floor plan is warm and inviting, featuring a custom fireplace with mantle, quartz counters, wood cabinetry, and a pantry off the kitchen leading to a dedicated laundry room. Outside, a saltwater pool and paver patio added in 2025 create a private oasis perfect for full-time living or generating exceptional rental income. A separate detached structure on the property opens the door to even more possibilities — artist studio, home office, she-shed, or additional guest accommodations. Already a proven rental performer before the pool was added, this property is primed for even stronger returns. Live here full time, rent it seasonally, or lease it annually — the choice is yours. Minutes to Downtown Sarasota, St. Armand's Circle, and Sarasota's famous Gulf beaches.
Listing Agent: Catherine Aganmayo (612-910-9915)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.