Location: Sarasota , 34231
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5474 RIVERBLUFF CIR #V35, SARASOTA, FL 34231
$219,900222 Days on yellowkey MLS ID: A4669393
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1120 Built: 1971 Tax: $2,363 (2024)Community: Strathmore Riverside IVilla
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,363
Elementary School: Phillippi Shores Elementary
High School: Riverview High
Tax Year: 2024
Middle School: Brookside Middle
Remarks: Welcome to Strathmore Riverside Villas, a vibrant 55+ community perfectly situated in the heart of Sarasota. This spacious two-bedroom, two-bath villa offers the ideal blend of comfort, convenience, and endless potential. Light, bright, and airy, the home features an open-concept layout with generous room sizes and an inviting flow throughout. The enclosed lanai, complete with both windows and screens, provides a wonderful year-round living space; perfect for morning coffee, relaxing afternoons, or entertaining friends. The villa also includes a one-car carport and a separate storage and laundry area, offering privacy, security, and plenty of extra space. With just a touch of personalization, this residence can truly shine. The community itself is beautifully maintained and lushly landscaped, creating a serene and welcoming atmosphere surrounded by green space. Strathmore Riverside Villas is known for its active lifestyle and warm sense of community. Residents enjoy a wealth of amenities, including a heated geothermal pool overlooking the marina, clubhouse, fitness center, library, meeting rooms, sauna, and billiards. There’s always something happening here; social events, card games, bingo nights, potlucks, concerts, dancing, and more. Boat docks are available on a first-come, first-served basis for just $1,344 per year, and the community is pet-friendly. The location couldn’t be better; just minutes from shopping, hospitals, and the world-famous Siesta Key Beach, as well as the rich cultural attractions of downtown Sarasota, including opera, ballet, symphony, and live theatre. Whether you’re looking for a full-time residence or a seasonal getaway, this villa lives like a single-family home and offers the perfect opportunity to enjoy Florida’s relaxed coastal lifestyle. Don’t wait; schedule your private tour today and discover the charm of Strathmore Riverside Villas.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Rachelle Golden (941-538-8998)
1621 MEMORY LN, SARASOTA, FL 34231
$3,980,000147 Days on yellowkey MLS ID: A4677041
Bed: 5 Bath: 7.0 Gar: 2 Liv Area Sq Ft: 4626 Built: 2027 Tax: $16,466 (2025)Community: Not Part Of A SubdivisionSpa: YesSingle Family
Taxes:$16,466
Elementary School: Gulf Gate Elementary
Tax Year: 2025
Remarks: Pre-Construction. To be built. 1621 Memory Lane presents a rare opportunity to build a custom bayfront estate on Little Sarasota Bay in the Bayview Acres neighborhood, one of Sarasota’s most strategically positioned mainland waterfront communities. Situated on a quiet no-through street south of Stickney Point Road and west of Tamiami Trail, this expansive .47-acre parcel offers approximately 100 feet of direct frontage on the bay and the scale to design a significant coastal residence with generous outdoor living areas, pool, and the ability to construct a private pier, subject to permitting. The property is offered as a vacant lot for $1,480,000 or as a to-be-built custom residence by The Vision Group priced at $3,980,000, providing flexibility for buyers to bring their own builder or move forward with a fully designed plan. The setting delivers privacy and calm while remaining just minutes from the south bridge to Siesta Key and equally convenient to downtown Sarasota’s dining, arts, and cultural amenities. Continued investment along the U.S. 41 and Siesta Drive corridor, including Benderson’s planned retail and mixed-use development, further strengthens the long-term appeal of this location. The property is especially well suited for buyers transitioning off the barrier islands who want mainland accessibility without sacrificing water views, as well as inland residents ready to elevate to a true bayfront setting without HOA constraints. With limited remaining buildable bayfront parcels of this size and frontage—and new construction next door on a comparable lot estimated at $6 million in value—the economics present a compelling opportunity to build at a meaningful discount to neighboring new construction.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Daniel Treiman (917-657-7495)
2802 SWIFTON DR #V102, SARASOTA, FL 34231
$195,00028 Days on yellowkey MLS ID: A4692282
2 Days Off yellowkey (back on 5/14/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 934 Built: 1971 Tax: $1,006 (2025)Community: Swifton VillasCondo
Taxes:$1,006
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Looking for simple, stress-free living minutes from the beach? This bright and airy end-unit in Swifton Villas offers the perfect blend of comfort and convenience. With 2 bedrooms, 2 baths, and a one-story layout, it’s ideal for easy everyday living or a seasonal getaway. Sip your morning coffee in the enclosed lanai, enjoy updated features like a refreshed kitchen and new A/C, and take advantage of a welcoming 55+ community with a pool, shuffleboard, and clubhouse with an active social scene. Other bonus features include tile floors, a retractable front door screen, sliding windows on the lanai, storm rated windows and new ceiling fans. Best of all—you’re just minutes from the beach and can walk to shopping, restaurants, and more. Low maintenance. Great location. Pet friendly. = Relaxed Florida lifestyle.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Marcia Nelson (941-321-6691)
3049 GYPSY ST, SARASOTA, FL 34231
$425,00025 Days on yellowkey MLS ID: A4693010
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 980 Built: 1981 Tax: $3,612 (2025)Community: Madison ParkSingle Family
Taxes:$3,612
Elementary School: Wilkinson Elementary
Remarks: Welcome to 3049 Gypsy Street, a beautifully updated, coastal-inspired retreat being offered turnkey furnished (minus personal property), making it the perfect opportunity for a first-time homebuyer, snowbird or savvy investor looking for immediate income potential. Previously operated as a highly rated Airbnb, this charming Sarasota home is move-in ready and set up to continue generating rental income from day one. Inside, discover a light and bright interior featuring luxury vinyl plank flooring throughout, a spacious living and dining area and a stunning remodeled kitchen complete with white cabinetry, stainless steel appliances, a farmhouse sink, a beautiful white 3D backsplash and all appliances included. The split-bedroom layout offers two spacious bedrooms and two completely renovated baths. The primary suite features a brand-new bath with a large walk-in shower, while the guest bedroom comfortably accommodates multiple guests with a full and twin bed. Outdoor living shines with a charming covered coastal-style lanai complete with a ceiling fan, shell paver patio area, fully fenced backyard, new landscaping and plenty of room for a future pool. There is also separate RV/boat parking on the side of the home for added flexibility or plenty of room for a pool. Additional highlights include a new roof (2022), a sewer connection completed in 2021, a one-car garage with a washer, dryer, utility sink and storage. Turnkey furnished opportunity: this was previously a successful Airbnb with a rental history. Ideally near all Sarasota has to offer, including world-famous beaches, dining, shopping, arts and entertainment, this adorable coastal getaway offers a blend of lifestyle and investment opportunity.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-907-9541)
Listing Agent: Jaci Krawtschenko (941-284-3789)
1860 SOUTHPOINTE DR, SARASOTA, FL 34231
$849,000440 Days on yellowkey MLS ID: A4643081
Bed: 0 Bath: 0.0 Gar: 2 Liv Area Sq Ft: 1993 Built: 1972Monthly Fee: $21 Tax: $6,409 (2023)Community: Southpointe ShoresApartment
Taxes:$6,409
Tax Year: 2023
Remarks: Property Size: 1,993 SF Total, +/- 996 SF Units This exceptional duplex offers an excellent investment opportunity in Sarasota, FL. With two spacious units, each featuring 2 bedrooms and 2 bathrooms, this property is perfect for owner-occupants or investors looking for rental income potential. The property boasts a rare RV full hookup pad, a two-car garage, and access to a community boat dock, adding to its unique appeal and versatility. 2 units, each with 2 bedrooms and 2 bathrooms RV full hookup pad 2-car garage Access to community boat dock
Listing is courtesy of: AMERICAN PROPERTY GROUP (941-923-0535)
Listing Agent: Leslye Seidel (941-544-8780)
1575 EASTBROOK DR, SARASOTA, FL 34231
$4,720,00025 Days on yellowkey MLS ID: A4692922
0 Days Off yellowkey (back on 5/13/2026)
Bed: 4 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4087 Built: 2025 Tax: $10,011 (2025)Community: Kentwood EstatesSpa: YesSingle Family
Taxes:$10,011
Remarks: Under contract-accepting backup offers. Behind one of Sarasota’s highly coveted Kentwood Estates, this extraordinary custom-built estate by award-winning Trinity Custom Homes delivers a level of luxury, craftsmanship, and architectural sophistication rarely seen in today’s market. From the moment you arrive along the sweeping circular driveway, the residence commands attention with its striking stone facade, dramatic rooflines, and manicured grounds, evoking the presence of a five-star private resort. Perfectly positioned on a serene lakefront homesite just moments from Siesta Key and Sarasota’s renowned waterfront lifestyle, this one-of-a-kind property was masterfully designed for the buyer who expects exceptional quality, timeless design, and elevated everyday living. Built with superior construction standards and cutting-edge technology, the home showcases Timberstrand engineered framing for long-term structural integrity, precision layout using a Trimble HP printer robot, and expert masonry by BMMI (Bob Miller Masonry), ensuring both durability and refined exterior detail. Andersen windows and exterior doors provide energy efficiency, storm resilience, and timeless design, while ISO insulation, enhances year-round comfort and performance. Inside, soaring vaulted ceilings with exposed architectural beams create a breathtaking first impression, while walls of glass frame tranquil water views and flood the home with natural light. The expansive open-concept floor plan blends warmth and sophistication, featuring wide-plank engineered hardwood flooring, solid custom poplar trim, solid-core Trustile interior doors, designer lighting, and curated high-end finishes throughout. The great room is anchored by a dramatic floor-to-ceiling stone fireplace, flowing seamlessly into the showpiece chef’s kitchen. Designed to rival the finest luxury residences, the gourmet kitchen features oversized dual waterfall islands, solid-ply Crystal Cabinetry, premium appliances, elegant stone countertops, designer backsplash details, double wall ovens, and a fully equipped wet bar—ideal for entertaining at the highest level. The luxurious owner’s retreat offers a private sanctuary with serene lake views, direct outdoor access, custom ceiling details, and a spa-inspired bath complete with dual vanities, a freestanding soaking tub, oversized walk-in shower featuring a Kerdi waterproofing system, and sophisticated designer finishes. Four additional bedrooms, a private den, and 5.5 beautifully appointed bathrooms provide exceptional comfort and flexibility for family and guests. Outdoor living is equally impressive, with an expansive screened lanai showcasing a resort-style pool and spa overlooking sparkling lake views and lush tropical landscaping. A fully equipped outdoor kitchen and multiple covered lounge areas create the perfect setting for both grand entertaining and quiet relaxation. Additional features include a whole-home generator, oversized garage space, and a PEX plumbing system for enhanced efficiency, durability, and long-term reliability. Located west of the Trail in one of Sarasota’s most desirable luxury neighborhoods, Kentwood Estates offers unparalleled proximity to Siesta Key Beach, Southside Village, downtown Sarasota, premier dining, shopping, marinas, golf courses, and top-rated schools. This is more than a home, it is a statement property defined by elite craftsmanship, advanced building techniques, and luxury living in the heart of Sarasota.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Adnan Dedic (941-726-2917)
5800 HOLLYWOOD BLVD #115, SARASOTA, FL 34231
$160,00033 Days on yellowkey MLS ID: A4691508
REDUCED by $10,000 (5.9%) on 05/07/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 679 Built: 1976 Tax: $2,106 (2025)Community: Baywood Colony Garden AptsCondo
Taxes:$2,106
Remarks: Discover your dream condo in the highly sought-after West of Trail location! Experience the ultimate Florida lifestyle with this stunning 1-bedroom, 1-bath condo just minutes from the pristine sands of Siesta Key. Situated on the first floor, this gem boasts brand-new luxury vinyl flooring, sleek stainless steel appliances, and new hurricane-impact windows. This condo offers modern comfort with peace of mind. Step outside, and you're only a short walk from the serene Phillippi Estate Park, where you can enjoy scenic nature trails, a fishing pier, a playground, and a charming gazebo—ideal for relaxing and soaking in the Florida lifestyle. Whether you are looking for an investment opportunity with great rental potential or a quiet retreat to call home, this condo offers unparalleled access to all the amenities, dining, shopping, and attractions Sarasota is known for. Don’t miss out on the chance to own a piece of paradise in one of the most desirable locations in town! NEW ROOF!! The seller is offering a generous $5,000 credit toward buyer closing costs or a mortgage rate buy-down.
Listing is courtesy of: RELAX PROPERTY GROUP, LLC (941-923-7200)
Listing Agent: Joleisy Machado-Gonzales (941-915-9251)
4891 PEREGRINE PT E, SARASOTA, FL 34231
$1,650,00057 Days on yellowkey MLS ID: A4688143
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3843 Built: 1983Monthly Fee: $29 Tax: $7,611 (2025)Community: The LandingsSingle Family
Taxes:$7,611
Remarks: Tucked within the winding, tree-lined streets of one of Sarasota's most coveted west of trail communities, this architectural gem offers a rare opportunity to own a signature custom home in The Landings. With over 3,800 square feet of living space, four bedrooms, four full baths, and a powder room, this 1983 residence is the epitome of elevated design - where bold architectural character meets serene, sanctuary-style living. Soaring vaulted ceilings and dramatic spiral stairwells set the tone from the moment you enter. An elevated library nook invites quiet retreat, while custom stained glass windows cast beautifully filtered light throughout the day. A dedicated meditation space adds a dimension of wellness rarely found in residential design - your own private escape to find balance and calm. The outdoor living experience has been thoughtfully reimagined. A resurfaced private pool anchors the expansive lanai, now complemented by a generous outdoor kitchen ideal for entertaining or simply savoring the Florida lifestyle in style. Life at The Landings extends well beyond your front door. Winding roads shaded by mature canopy trees, neighborhood lakes, parks, and nature trails create an idyllic backdrop for morning walks, cycling, and quiet reflection. Residents enjoy direct access to Roberts Bay, and the community's optional Racquet Club offers swimming, tennis, and lessons just a short bike ride away — a lifestyle as active or as tranquil as you choose. This is more than a home. It is a retreat, a statement, and a community.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Mickey Kiernan (941-402-9115)
1899 BUCCANEER CIR, SARASOTA, FL 34231
$1,749,900559 Days on yellowkey MLS ID: A4629706
3 Days Off yellowkey (back on 5/11/2026)
REDUCED by $250,000 (12.5%) on 04/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2135 Built: 1986Monthly Fee: $58 Tax: $12,833 (2024)Community: Buccaneer BaySingle Family
Taxes:$12,833
Remarks: Another STUNNING RENOVATION by Mako Homes! This gorgeous WATERFRONT residence is a true masterpiece, featuring a new 8,000-pound boat lift with NO BRIDGES to the bay, providing direct access to the newly re-opened Midnight Pass in just 10 minutes from your dock. Designed with style, comfort, entertaining, and privacy in mind, this home has been completely transformed. The spacious, OPEN KITCHEN is a chef’s dream, equipped with top-of-the-line appliances and seamlessly connected to a welcoming family area complete with a wet bar—perfect for entertaining guests. A large, ELEGANT FORMAL LIVING ROOM adds to the home's inviting and luxurious atmosphere. With COMPREHENSIVE UPGRADES throughout, you’ll enjoy peace of mind for years to come. New PEX waterlines, an On-demand water heater, a durable STANDING SEAM METAL ROOF, and IMPACT windows ensure long-term reliability. The newly VAULTED ceilings and fully replaced INSULATED DUCTWORK enhance the air conditioning system’s efficiency, while a complete overhaul of the electrical system includes modern, high-end fixtures. Step outside to your PRIVATE OASIS: a covered patio overlooking a huge pool with a new pebble tech coating and stylish tiled decking. The outdoor space continues with an open PAVER BRICK PATIO, leading to a lighted staircase down to the dock, which is equipped with electric and water hookups for ultimate convenience. As you arrive, the long, NEW and SEALED driveway welcomes you to the pristine, SOPHISTICATED LANDSCAPING designed for both beauty and privacy. The property’s lush greenery is maintained effortlessly with a NEW WELL and IRRIGATION system covering the 20,000+ square foot lot. Nestled in the serene neighborhood of Buccaneer Bay, this home is just minutes from major shopping destinations, restaurants and the world-famous Siesta Key Beach, offering the best of waterfront living in a prime location. Home is HIGH & DRY in ZONE X with NO DAMAGE FROM RECENT STORMS!
Listing is courtesy of: LOYD ROBBINS & CO. LLC (941-957-9300)
Listing Agent: Jeff Cashmore (941-356-5780)
2227-2229 MONTCLAIR DR #1&2, SARASOTA, FL 34231
$800,000147 Days on yellowkey MLS ID: A4677183
REDUCED by $25,000 (3.0%) on 05/06/2026
Bed: 6 Bath: 0.0 Gar: 2 Liv Area Sq Ft: 2118 Built: 1970 Tax: $7,681 (2025)Community: Monticello Unit 1Spa: NoApartment
Taxes:$7,681
Remarks: This nicely updated two-unit duplex in the desirable Phillippe Gardens community on Coquina Island offers excellent income potential in a highly sought-after location. Situated on a generous corner lot, each unit features 3 bedrooms and 2 bathrooms, including a private primary bath, along with a newer eat-in kitchen that flows seamlessly into the living room. UPDATES INCLUDE- 3 NEW BATHROOMS, NEW QUARTZ COUNTERTOPS, NEW FLOORS, NEW GARAGE DOORS. Both units include a private backyard, an attached garage, and the convenience of a large side drive with ample parking. The property is ideally located just 10 minutes from Siesta Key Beach, 12 minutes from Siesta Key Village, and less than 20 minutes from major shopping, downtown Sarasota, and top local attractions. With easy access to US-41, waterfront dining, vibrant nightlife, and award-winning Gulf beaches, this turn-key duplex is perfectly positioned for strong rental demand. Priced to sell, it presents a rare opportunity for investors seeking a ready-to-go property in an exceptional Sarasota location.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Lisa Sanders (773-398-0378)
5571 RIVERBLUFF CIR #V1, SARASOTA, FL 34231
$127,500210 Days on yellowkey MLS ID: C7517249
0 Days Off yellowkey (back on 5/12/2026)
REDUCED by $12,400 (8.9%) on 05/07/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1120 Built: 1971 Tax: $2,543 (2024)Community: Strathmore Riverside ICondo
Taxes:$2,543
Remarks: WELCOME HOME to your 55+ community with your end unit Villa that offers you water/boating access to Philippi Creek then on to Bay, Intracoastal and Gulf if you so choose, as well as community pool, clubhouse and more all in the heart of Sarasota where you'll find so much to do. This unit is waiting for you to make it sparkle once again. One car carport offers storage room behind which houses your laundry area too. The primary bedroom has en suite with tub/shower combo and walk in closet. You'll enjoy the easy flow floorplan too. This is worth your time to look, just might be what you have in mind!
Listing is courtesy of: OCEAN PARTNERS REAL ESTATE (941-627-6232)
Listing Agent: Bradley Geddeis (941-627-6232)
4689 PINE HARRIER DR, SARASOTA, FL 34231
$1,599,50026 Days on yellowkey MLS ID: A4692523
1 Days Off yellowkey (back on 5/12/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3103 Built: 1986Monthly Fee: $29 Tax: $7,212 (2025)Community: The LandingsSpa: NoSingle Family
Taxes:$7,212
Remarks: Under contract-accepting backup offers. Multiple Offers. Seller requests highest and best offers by 8pm on May 10. Nestled behind the gates of The Landings, one of the only gated communities "West of the Trail", this custom Florida-style home offers the perfect blend of timeless elegance, spacious living, and an exceptional Sarasota lifestyle. Situated on a desirable corner lot with easy access to the members-only gate, this beautifully updated home spans more than 3,100 square feet and features four bedrooms, three-and-a-half baths, a three-car garage, bonus room, and an upstairs loft area ideal for flexible living. Designed with an open, airy feel and soaring high ceilings, the home is filled with natural light and inviting living spaces perfect for both everyday comfort and entertaining. The expansive screened lanai showcases two separate sitting areas, an outdoor kitchen, a large heated pool with recent resurfacing, and views of the spacious backyard, the benefits of being a corner lot, creating a true private retreat. Inside, the thoughtfully designed floor plan features a rare first-floor primary suite, a highly sought-after feature for a two-story home in The Landings. The updated kitchen is the heart of the home, complete with a large center island perfect for gathering with family and friends while creating lasting memories. Updated bathrooms, a cozy fireplace in the living room, fresh interior and exterior paint, further enhance the move-in-ready appeal of this exceptional property. Residents of The Landings enjoy tree-canopied streets, a private nature trail leading to Roberts Bay, and optional membership to the Landings Racquet Club, featuring tennis, pickle ball, a heated pool, fitness center, and clubhouse. This prestigious gated community of 702 residences borders the Intracoastal Waterway and spans 280 acres with stand-alone homes, villas, and town-homes surrounded by 75 acres of protected mangroves, nature preserves, walking trails, a gazebo, kayak launch, and butterfly garden. Take your golf cart to the Landings Shopping Center which features, Publix grocery store, Starbucks, and numerous dining options from breakfast hot spots to outstanding seafood options. Ideally located near A-rated schools, Southside Village, Sarasota Memorial Hospital, and Sarasota’s renowned dining, arts, and waterfront attractions, this is a rare opportunity to own a beautifully updated home in one of Sarasota’s most desirable gated communities. Located in flood zone X, the highest zone, no flood insurance required.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Thomas Hedge, Jr (941-587-6660)
2630 WOODGATE LN #G3, SARASOTA, FL 34231
$189,000250 Days on yellowkey MLS ID: TB8431315
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1100 Built: 1981 Tax: $1,248 (2024)Community: Pinewood Village ViCondo
Taxes:$1,248
Remarks: $$ 10,000.00 in closing cost's paid for by the SELLER. Like new and upgraded gorgeous condo. Minutes from world famous Siesta Key Beach and safely located in flood zone X. All new vinyl plank flooring in living areas and new carpet in bedrooms. Both bathrooms are newly renovated, freshly painted inside and out, along with a total makeover of the kitchen in 2025. Located in the rear of the development this condo is very quiet and secure. New washer and dryer, make this as good as a new unit. Ceiling fans and skylights keep it light and bright inside. Community heated pool and fitness center are open to the residents at their leisure. Clubhouse includes kitchen, fitness center, pool table and rest rooms with showers. Lanai features fully enclosed glass windows with screens, new storm doors front and rear. Gardener's paradise in the rear with lush tropical plants. In front enjoy your reserved private parking spot. Close to shopping and some of the best restaurants in Sarasota.
Listing is courtesy of: DENNIS REALTY & INV. CORP. (813-949-7444)
Listing Agent: John Pinta (813-390-4918)
1740 ASSISI DR, SARASOTA, FL 34231
$1,370,00049 Days on yellowkey MLS ID: A4689889
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3357 Built: 2027Monthly Fee: $320 Tax: $2,045 (2025)Community: Portofino On The BaySpa: YesSingle Family
Taxes:$2,045
Remarks: Pre-Construction. To be built. Located in the highly sought-after Portofino on the Bay neighborhood in Sarasota, this cleared homesite presents a rare opportunity to build your dream home in one of the area’s most desirable coastal communities. The property has already been cleared and is ready for construction, offering a smooth and convenient start for your custom build. A builder of your choice can be selected, however plans have been made for this lot - an option of a 3,357 sq. ft. home, providing the opportunity to streamline the building process with a thoughtfully designed home. Buyers may choose to utilize the existing plans or customize them to suit their vision and lifestyle. Building plans must be approved by the board group of the community. The property is also located within the district for the highly regarded Pine View School, along with other highly rated public and private schools nearby. This private and gated neighborhood is great for boaters, offering community deeded access to the bay and a community day dock, that is available upon reservation. Enjoy direct access to the Intracoastal Waterway. Boat slips could potentially become available for purchase if a community member is selling. Located just 2 miles from downtown Sarasota, residents enjoy quick access to vibrant dining, shopping, and entertainment while still enjoying the privacy and tranquility of this waterfront-friendly community.
Listing is courtesy of: PHAM REALTY GROUP LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
1970 DEBBIE ST, SARASOTA, FL 34231
$515,00022 Days on yellowkey MLS ID: A4693170
0 Days Off yellowkey (back on 5/11/2026)
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1880 Built: 1978 Tax: $4,740 (2025)Community: North Vamo Sub 2Apartment
Taxes:$4,740
Remarks: Under contract-accepting backup offers. Under contract-accepting backup offers. Don’t miss this exceptional opportunity to own an updated, income-producing duplex. Each unit offers its own private entrance, opening into a bright and functional living, dining, and kitchen space—perfect for comfortable everyday living or attracting quality tenants. Both units feature 2 bedrooms and 2 full bathrooms, providing an ideal layout for privacy and convenience. Step outside to enjoy a covered back patio for each unit, creating the perfect spot to relax or entertain. Location truly sets this property apart—situated just minutes from shopping, dining, and popular attractions, and only a short drive to Siesta Key. Positioned west of the trail, this highly sought-after area continues to hold strong value, making it a smart addition to any investment portfolio. Whether you’re looking to generate rental income, or expand your real estate holdings, this duplex offers versatility, location, and long-term potential.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Lily Lopez (941-586-0082)
1705 FIELD RD, SARASOTA, FL 34231
$2,295,000209 Days on yellowkey MLS ID: A4671008
1 Days Off yellowkey (back on 5/11/2026)
REDUCED by $204,000 (8.2%) on 05/06/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2409 Built: 2020 Tax: $9,575 (2024)Community: Oyster Bay EstatesSingle Family
Taxes:$9,575
Remarks: Under contract-accepting backup offers. Welcome to this stunning, fully reimagined residence in Oyster Bay Estates, one of Sarasota’s most coveted West of the Trail neighborhoods. Renovated down to the studs with an effective build date of 2020, this exceptional home blends timeless coastal elegance with modern sophistication, showcasing the level of craftsmanship and finish quality typically found in five million dollar plus luxury properties. Thoughtfully designed throughout, the home features wide-plank wood flooring, custom millwork, and an open-concept floor plan designed for both everyday living and effortless entertaining. The gourmet kitchen serves as the centerpiece of the home, offering designer cabinetry, quartz countertops, an oversized island, Sub-Zero and Wolf appliances, and luxury Perrin & Rowe fixtures. The residence includes four spacious bedrooms, three full bathrooms, and two half baths, each beautifully finished with premium materials and spa-inspired details. The beachy character continues with an outdoor shower. Major systems and components have all been replaced, including the electrical, plumbing, HVAC systems, roof, siding, and hurricane-impact windows and doors, including the garage door, providing both comfort and peace of mind. Located in Flood Zone X, flood insurance is not required. Privately set back from the street, the property offers a quiet, resort-like setting with lush new tropical landscaping featuring coconut palms, cabbage palms, orchid trees, pitch apple hedges, and bougainvillea to name a few. The outdoor spaces have been completely transformed with shell-finished hardscape, new patios, elegant walkways, and a private irrigation well. Offered fully furnished, this move-in-ready home is ideally located just moments from downtown Sarasota, St. Armands Circle, world-renowned beaches, shopping, dining, top-rated schools, and less than a block from the historic The Field Club. Buyer and Buyer’s Agent to verify all room dimensions.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Albert Joerger (941-685-6145)
2852 CAPTIVA DR, SARASOTA, FL 34231
$559,000294 Days on yellowkey MLS ID: A4661671
REDUCED by $16,000 (2.8%) on 04/08/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2033 Built: 1975Monthly Fee: $4 Tax: $5,128 (2025)Community: Gulf Gate WoodsSpa: NoSingle Family
Taxes:$5,128
Remarks: Under contract-accepting backup offers. NEW PRICE ON THIS BEAUTIFULLY UPDATED AND MOVE-IN READY GULF GATE POOL HOME WITH 2025 TILE ROOF! ADDITIONAL 2025/26 UPDATES INCLUDE UPGRADED ELECTRICAL SERVICE, NEW DUCTWORK, CARPET, BATHS, EXTERIOR/INTERIOR PAINT, DISHWASHER, DRIVEWAY, FENCE, LANDSCAPING AND MORE! Located in the sought-after Gulf Gate Woods community, this beautifully refreshed 3-bedroom, 2 full bathroom residence blends timeless design with modern upgrades, all nestled just minutes from world-renowned Siesta Key Beach. The bright and spacious living room welcomes you with natural light and new neutral tone plush carpet. The open-concept kitchen features a just completed raised ceiling with recessed lighting and additional 2017 improvements including stainless steel appliances, soft close cabinetry, and granite countertop, and flows seamlessly into a generous breakfast room and separate dining room too! The thoughtful split-bedroom floor plan ensures privacy, with the primary suite positioned separately from the guest bedrooms. The primary bedroom features a renovated en-suite bath with sleek subway tile shower enclosure, on-trend black fixtures, new floating vanity and modern finishes. Two additional bedrooms are located on the opposite wing and share an updated full bath with a granite topped vanity. The additional 24x10 bonus room is a great space for entertaining or relaxation, with windows out to your own private oasis which includes the sparkling pool and screened lanai. A 2023 water heater ensures energy efficiency, while the spacious interior laundry room adds everyday convenience. The prior owner replumbed the home with PVC pipes. The attached two-car garage includes abundant cabinetry, ideal for storage and organization. This home is in the X flood zone and is high and dry. Gulf Gate Woods is a well-established neighborhood known for its sidewalks, streetlights, and friendly sense of community. Zoned for A-rated schools, this prime Sarasota location places you within 10 minutes of Siesta Key Beach, downtown Sarasota, the Legacy Trail, golf courses, fitness centers, Sarasota Memorial Hospital, fine dining, UTC and the charming shops and restaurants of Gulf Gate Village. Whether you're seeking a full-time residence, seasonal getaway, or a smart investment, this home offers flexibility and would also make an excellent option for a long or short-term rental.
Listing Agent: Lenore Treiman (941-356-9642)
2544 ORSOVA WAY, SARASOTA, FL 34231
$495,00026 Days on yellowkey MLS ID: A4692439
0 Days Off yellowkey (back on 5/8/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1545 Built: 1964 Tax: $4,594 (2025)Community: Phillippi Gardens 14Spa: NoSingle Family
Taxes:$4,594
Remarks: Tucked away in one of South Sarasota's most coveted neighborhoods, this exceptional property offers the rare combination of tranquil privacy and unbeatable convenience. Nestled just off Constitution Boulevard south of Phillippi Creek, the setting feels like a retreat — yet world-class dining, boutique shopping, and the pristine shores of Siesta Key's award-winning beach are all within a mile from your front door. Inside, every detail has been thoughtfully curated for effortless, modern living. Sleek wall-to-wall ceramic tile flows throughout the home, while a fully upgraded second bathroom showcases premium finishes with no detail overlooked. The master bath has also been beautifully refreshed with new tile and cabinetry, delivering a spa-like feel you'll love coming home to. Step outside to your own private oasis — a spacious heated pool, recently resurfaced and encased in a brand-new screen enclosure, perfect for year-round entertaining. Host effortlessly, unwind completely, and create lasting memories in a backyard built for both. Peace of mind comes standard here. A brand-new roof (Fall 2025) backed by a 15-year warranty, new hurricane-impact windows (Fall 2025), fresh exterior paint, and manicured landscaping mean this home is truly move-in ready from day one. An oversized two-car garage rounds out the package with the storage and functionality today's buyers demand. BEST OF ALL— NO HOA, NO DEED RESTICTIONS, and NO CDD. This is the freedom to live on your terms, in a home that has it all.
Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)
Listing Agent: Aaron Wittenstein (941-299-1151)
5476 SWIFT RD #19, SARASOTA, FL 34231
$147,90048 Days on yellowkey MLS ID: A4689984
REDUCED by $7,000 (4.5%) on 05/11/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1095 Built: 1981 Tax: $2,164 (2025)Community: Imperial PlaceCondo
Taxes:$2,164
Middle School: Sarasota Middle
Remarks: Live the Florida lifestyle you’ve been dreaming of—just minutes from the powdery white sands of Siesta Key Beach. This rarely available ground-floor, two-bedroom, two-bath end-unit condo combines location, upgrades, and effortless living in one exceptional package. From the moment you step inside, you’ll notice the light-filled, airy feel enhanced by extra windows—an exclusive perk of end-unit living—and a desirable south-facing position. This home features newer luxury vinyl flooring, newer appliances, impact windows (2019), AC (2020), and a brand-new roof (2025), offering true peace of mind. The open-concept layout seamlessly connects the living, dining, and kitchen areas—perfect for entertaining or simply relaxing after a day at the beach. Step outside through sliding glass doors to your oversized screened-in patio, where morning coffee and evening breezes become part of your daily routine. Located in Imperial Place, residents enjoy a community pool and convenient access to nearby attractions all while being just minutes from shopping, dining, and everyday essentials at Detwiler's Farm Market and the nearby Costco. Plus, you’re within easy reach of Downtown Sarasota, Venice, Sarasota-Bradenton International Airport, The Mall at University Town Center, and the natural beauty of Myakka River State Park. Whether you’re searching for a full-time residence, seasonal escape, or income-producing investment, this is the kind of opportunity that doesn’t last.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Daniel Jasmer (941-284-9893)
5420 EAGLES POINT CIR #106, SARASOTA, FL 34231
$625,00085 Days on yellowkey MLS ID: A4684787
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2021 Built: 1993 Tax: $3,692 (2025)Community: Eagles Point At The Landings 1Condo
Taxes:$3,692
Remarks: One or more photo(s) has been virtually staged. Experience the relaxed elegance of life in Eagles Point at The Landings, where beautiful waterfront surroundings, vibrant amenities, and breathtaking sunsets create a lifestyle that feels like a year-round retreat. Positioned to capture colorful nightly skies and holiday fireworks, this first-floor corner residence invites you to enjoy the view from the comfort of your enclosed Florida Room, complete with hurricane-rated sliders and a western-exposure balcony. Just outside, an open terrace offers additional space for outdoor lounging, morning coffee, or evening gatherings. Inside, the 3-bedroom residence feels light, airy, and inviting, offering spacious living areas and a thoughtfully designed layout. The open dining and living areas flow seamlessly together, creating an ideal setting for entertaining or relaxed everyday living. Elegant touches elevate the space, including Brazilian cherry wood flooring, crown molding, plantation shutters, Luminette drapes, and a striking Swarovski crystal chandelier in the dining room. The well-appointed kitchen blends style and function with a granite-topped island, stainless steel appliances, white raised-panel cabinetry, abundant storage, a reverse osmosis water system, and a cozy eat-in area for casual dining. A convenient pass-through keeps the kitchen connected to the dining space. Privately situated off the living room, the owner's retreat also opens to the Florida Room, allowing you to wake up to peaceful views each morning. The spacious suite includes a walk-in fitted closet, dual-sink vanity, garden tub, and separate shower. Two additional guest bedrooms offer eastern exposures, welcoming the warm glow of the morning sun. Additional conveniences include a spacious laundry room with utility sink and extra storage, an assigned parking space in the secure garage, and a private storage room. Pets up to 25 pounds are welcome. Life in Eagles Point offers more than a beautiful home —it’s a lifestyle. Residents enjoy a private community pool and grilling area, perfect for relaxed afternoons with neighbors and friends. Beyond Eagles Point, The Landings is a gated community known for its vibrant social atmosphere and exceptional amenities. Residents enjoy membership to the Landings Racquet Club, featuring eight Har-Tru tennis courts, pickleball, a resort-style pool and spa, fitness center, library, and community room. Nature lovers will appreciate the scenic trail leading to the fishing pier on the Intracoastal Waterway, along with kayak storage and launch access. Whether you’re seeking a full-time residence or the perfect winter retreat, this home offers the opportunity to embrace The Landings lifestyle—where sunsets, recreation, and coastal serenity become part of everyday living.
Listing Agent: Dianne Anderson (941-350-3513)
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