Location: Sarasota , 34239
Do Not Show Listings
2160 SUNNYSIDE PL, SARASOTA, FL 34239
$875,000131 Days on yellowkey MLS ID: A4674367
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1542 Built: 1954 Tax: $8,511 (2024)Community: Hibiscus Park 2Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,511
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Stylish and turnkey home with the perfect blend of mid-century charm and modern updates. Located in the desirable Sunnyside Park neighborhood, the property features an open, light-filled layout with a renovated kitchen, granite countertops, stainless steel appliances, and a large breakfast bar that flows into the dining and living areas. The spacious primary suite includes a walk-in closet and an updated en-suite bath with double vanity and walk-in shower. Two additional guest bedrooms provide ideal flexibility for family, visitors, or a home office. A second full bath features a deep soaking tub and modern finishes. Step outside to your private tropical oasis with a saltwater pool, landscaped and fully fenced backyard, and a mini putting green - perfect for relaxing or entertaining. The home is offered furnished and includes an in-unit laundry area and driveway parking for two vehicles. Tankless water heater. Just minutes to Siesta Key Beach, downtown Sarasota, St. Armands Circle, dining, shopping, and more. Move-in ready with excellent potential as a primary residence, seasonal retreat, or investment property with weekly rentals allowed.
Listing is courtesy of: ORQUERA FLORIDA INVESTMENTS (941-203-8135)
Listing Agent: Greg Orquera (941-735-9098)
3360 S OSPREY AVE #201B, SARASOTA, FL 34239
$249,000158 Days on yellowkey MLS ID: A4671792
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1122 Built: 1969 Tax: $3,282 (2025)Community: Bermuda On OspreyCondo
Taxes:$3,282
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: One step away from Siesta Key, Sarasota Memorial and Hillview. West of the trail. Beautiful condo in Oasis on Osprey. Enjoy the community pool before you head to the beach.2 bedrooms, 2 bathrooms. large living area. Screened lanai. All tiled for easy maintenance. Granite countertop in kitchen. AC 2020.
Listing is courtesy of: INVESTUS REALTY LLC (941-538-2010)
Listing Agent: Vincent Ricaud (941-538-2010)
3118 KEY WAY, SARASOTA, FL 34239
$599,00043 Days on yellowkey MLS ID: A4685119
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2370 Built: 1961 Tax: $2,942 (2025)Community: SouthgateSpa: NoSingle Family
Taxes:$2,942
Elementary School: Wilkinson Elementary
Remarks: One or more photo(s) has been virtually staged. Beautifully updated 4-bedroom, 2-bath pool home in the desirable Southgate neighborhood of Sarasota offering the ideal blend of indoor comfort and outdoor Florida living. The home features a bright open layout with expansive pocket sliding glass doors that fully open to an oversized open-air pool and patio, perfect for entertaining and relaxing. The updated kitchen includes extensive custom cabinetry with built-in pantry storage and a discreetly integrated laundry area. The home offers four spacious bedrooms and two bathrooms, including a guest bath with a soaking tub. Outside, the property features a large additional paved parking pad along with the driveway and garage, providing ample space for multiple vehicles and recreational equipment. With minimal deed restrictions, the property allows RV and boat parking, with additional space along the side of the home. The backyard also includes a custom playground area. Conveniently located just minutes from Siesta Key Beach, downtown Sarasota, shopping, dining, and parks.
Listing is courtesy of: PREMIER AGENT NETWORK (877-663-9366)
Listing Agent: Stephanie Hawkins (941-587-4337)
1240 HILLVIEW DR, SARASOTA, FL 34239
$16,950,00010 Days on yellowkey MLS ID: A4688990
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4852 Built: 1992 Tax: $80,000 (2025)Community: Harbor AcresSpa: YesSingle Family
Taxes:$80,000
Middle School: Sarasota Middle
Remarks: Introducing “Gatsby Manor,” set along Hillview Drive, one of Sarasota’s most coveted bayfront addresses, often compared to Port Royal for its exclusivity and waterfront lifestyle, this rare Harbor Acres estate property spans nearly three-quarters of an acre on deep, boatable water with sweeping, unobstructed Sarasota Bay views stretching south toward Siesta Key and the Gulf of Mexico, representing one of the neighborhood’s most distinguished open-bay offerings where only a select few residences achieve true estate scale. Encompassing more than 8,000 square feet of air-conditioned space with four bedrooms and three-and-a-half baths. The residence is complemented by a grand motor court accommodating 15+ vehicles beneath a canopy of majestic grand oaks. Privately approached through wrought-iron gates and a sweeping circular drive anchored by a multi-tiered fountain, the home opens to a dramatic two-story foyer framing the water beyond. Interiors are defined by soaring ceilings up to 22 ft. in height, exceptional millwork, multiple fireplaces, a striking two-story wood-paneled library, formal dining with 12-foot ceilings, and a wetbar—perfectly blending elegant entertaining with comfortable daily living. The chef’s kitchen is designed to support both everyday living and large-scale gatherings, featuring double 36-inch Sub-Zero refrigerators with dual freezer drawers, two dishwashers, and a 60-inch Wolf gas range with six burners and infrared dual griddle. The owner’s suite occupies the entire east wing of the main living level, creating a private waterfront retreat complete with a gas fireplace, sitting area overlooking the pool and bay, dual walk-in closets, and a spa-inspired bath highlighted by a sculptural copper soaking tub, dual vanities, and a dedicated luxury makeup area. Upstairs, a second primary-style suite and two additional guest bedrooms are accessed via the grand staircase or three-stop elevator, offering privacy and flexibility for family and guests. The 3,800+ square-foot ground-level bonus area serves as the home’s ultimate entertaining environment, featuring a remarkable speakeasy lounge and an impressive 700+ bottle wine room. This expansive space functions as a true extension of the residence’s living experience—ideal for hosting gatherings, intimate evenings, or celebrations on a grand scale. Outdoor living is equally exceptional, centered around an expansive marble terrace surrounding the 25’ × 60’ heated saltwater pool with integrated sun shelf and spa. A brand new deep-water dock with a 20,000 lb. boat lift and seawall replaced in 2017 further enhance the property’s boating capabilities and long-term value. Additional highlights include hurricane-rated garage doors, elevator access to all three levels, a drive-through three-car garage, and extensive storage throughout. Perfectly positioned just a short stroll to Southside Village’s restaurants and boutiques, minutes from downtown Sarasota’s celebrated arts and cultural district, and only four blocks from Sarasota Memorial Hospital. Gatsby Manor offers a truly rare opportunity to enjoy estate-scale open-bay living with deep water, privacy, and exceptional walkability in one of Sarasota’s most prestigious waterfront neighborhoods.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
3230 VILLAGE GREEN DR #1032, SARASOTA, FL 34239
$195,00057 Days on yellowkey MLS ID: A4683197
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1419 Built: 1971 Tax: $3,030 (2025)Community: South Gate Village Green 10Condo
Taxes:$3,030
Remarks: Welcome to a classic Florida home that perfectly blends comfort, style, and functionality. With its solid construction and timeless character, the home blends classic design with the potential for modern updates, making it perfect for buyers looking to personalize their space. Spacious living areas, abundant natural light, and a functional layout create an inviting atmosphere ideal for both relaxing and entertaining. The open-concept layout creates a seamless flow between the kitchen, dining, and living areas, making it all the more inviting. Village Green is a 55+ community that has a ton of amenities. Right on the other side of the neighborhood is even an executive golf course that can meet all your golfing needs.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: James Graves (678-817-8166)
2625 COLONY TER, SARASOTA, FL 34239
$2,650,00029 Days on yellowkey MLS ID: A4686022
1 Days Off yellowkey (back on 4/8/2026)
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3634 Built: 2007 Tax: $16,973 (2025)Community: Bay View Heights AddSpa: YesSingle Family
Taxes:$16,973
Remarks: Upon entering this impeccably crafted residence, you are immediately greeted by a refined level of finish and thoughtful design. Rich hardwood flooring flows seamlessly throughout the main living areas, complemented by intricate custom millwork, elegant moldings, and double tray ceilings that enhance the home’s architectural character. Designed with intention, this 4-bedroom, 4-bath residence—featuring two bedrooms currently utilized as a den and one as a sitting room—along with a versatile bonus room ideal as a fifth bedroom, office, or private gym, offers effortless single-level living with an exceptional sense of space and functionality. As you enter, a formal sitting area anchored by a detailed fireplace creates an inviting first impression, complemented by an adjacent dedicated dining room and an elegant wet bar—perfect for entertaining. The kitchen is a true statement of both style and function, featuring artisan granite, two expansive islands offering generous space for cooking, gathering, casual seating, and designer backsplash detailing. A full suite of top-tier stainless steel appliances, including dual Liebherr refrigerators, an induction cooktop, and a built-in oven and microwave, is seamlessly integrated. Reverse osmosis filtration at the sink, along with a whole-house water filtration system, enhances everyday living. The spacious family room is designed for comfort, offering expansive views of the pool and lush Florida-native landscape, creating a seamless indoor-outdoor living experience. The primary suite is a luxurious private retreat, offering direct access to the pool, three spacious walk-in closets, and a spa-inspired bath adorned with exquisite custom stone finishes. The primary bathroom is thoughtfully designed with two separate vanities and generous counter space. Meticulously maintained and extensively upgraded, the home offers a level of efficiency and ease. Recent improvements include a new roof (2023), two new Lennox air conditioning systems (2023–2024), Storm Smart hurricane shutters, and hurricane-rated garage doors. A whole-home generator and multiple propane tanks provide added peace of mind, while energy-efficient heat pump systems service the pool heater, water heater, and HVAC. Outdoor living is equally impressive, with a beautifully updated pool area featuring a fully refurbished enclosure, upgraded automation system, and pool heater. An Artisan infrared grill connected to a permanent propane source creates an ideal, relaxed setting for entertaining, surrounded by Florida-friendly native landscaping and ambient landscape lighting. Additional enhancements include a drip irrigation system with a separate meter, an upgraded security system with cameras, and UniFi Wi-Fi extenders for seamless connectivity throughout the home. The three-car garage is as functional as it is polished, featuring an epoxy-coated floor, built-in cabinetry, and overhead gantry storage systems. Throughout the home, you’ll find abundant storage space with custom-built-in cabinetry thoughtfully integrated for easy everyday living. Ideally situated in the highly coveted West of Trail enclave of Bayview Heights, this custom-built home offers an exceptional lifestyle. Located on a rare dead-end street just one block from the bay, and within minutes of downtown Sarasota, Southside Village, and the area’s renowned beaches, it also lies within top-rated school districts—an unparalleled combination of privacy, convenience, and prestige.
Listing Agent: Courtney Tarantino (941-893-7203)
1400 SIESTA DR, SARASOTA, FL 34239
$4,500,00053 Days on yellowkey MLS ID: A4678496
Bed: 3 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 4660 Built: 1978 Tax: $22,924 (2025)Community: Acreage & UnrecSpa: YesSingle Family
Taxes:$22,924
Remarks: Welcome to 1400 Siesta Drive, where refined waterfront living becomes your everyday reality. This home is quietly tucked away behind a gated entrance, with an additional secondary gate providing exclusive access to the residence. Thoughtfully designed to embrace breathtaking, unobstructed views of Sarasota Bay, this modern residence is a showcase of light, space, and coastal elegance. Expansive floor-to-ceiling windows frame the ever-changing scenery, offering front-row views of passing boats and unforgettable sunsets from nearly every room. The primary suite is a private sanctuary, featuring a generous walk-in closet, a spa-inspired ensuite bath, and a dedicated office—each enhanced by stunning bay views. Outdoors, your personal oasis awaits with a heated pool, abundant sun-drenched lounging space, and a newly constructed dock ready for effortless boating and waterfront adventures. Ideally located near Sarasota’s world-class dining, shopping, and cultural attractions, this exceptional bayfront retreat offers the perfect balance of privacy and convenience. Offered turn-key furnished, this is a rare opportunity to step seamlessly into an elevated waterfront lifestyle.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Matthew Voss (941-402-8799)
2224 BAHIA VISTA ST #E1, SARASOTA, FL 34239
$200,000181 Days on yellowkey MLS ID: A4668974
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 982 Built: 1979 Tax: $2,460 (2024)Community: Cordova Gardens IiCondo
Taxes:$2,460
Elementary School: Alta Vista Elementary
Remarks: Motivated sellers are ready to make a deal—bring your offer! This beautifully updated ground-floor condo in the desirable Cordova Gardens community is priced to move and offers the perfect blend of comfort, location, and value right in the heart of Sarasota. Whether you’re downsizing, investing, or searching for your first Florida home, this is an opportunity you won’t want to miss. Step inside and immediately feel at home in the bright, open layout featuring modern luxury vinyl flooring and plenty of natural light. The renovated kitchen showcases granite countertops, sleek gray cabinetry, and generous storage, seamlessly connecting to the dining and living areas for easy entertaining. Both bathrooms have been tastefully refreshed with modern finishes, and the split-bedroom floor plan provides privacy for guests or a dedicated home office. Through the sliding glass doors, enjoy your private screened lanai overlooking lush landscaping—a serene spot for morning coffee or relaxing after a day at the beach. With assigned parking right outside your door and a ground-floor location, convenience is built into every detail. Living at Cordova Gardens means worry-free homeownership. The monthly fee covers water, sewer, trash, internet, landscaping, pest control, and exterior maintenance, along with access to the community pool, clubhouse, and gathering spaces—everything you need for easy Sarasota living. Location couldn’t be better—just minutes from downtown Sarasota, Sarasota Memorial Hospital, Lido Beach, Payne Park, the Legacy Trail, and the Sarasota Art Museum. Top-rated schools like Alta Vista Elementary, Brookside Middle, and Sarasota High are nearby, and you’re within walking distance of local favorites such as Yoder’s Fresh Market, Big Olaf Ice Cream, and the YMCA. This condo truly checks every box—style, location, and value—with owners eager to sell and ready to review all offers. Don’t wait—schedule your private showing today and make this Sarasota gem your next home before it’s gone!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Rachel Tritschler (941-993-5892)
3837 CAMINO REAL, SARASOTA, FL 34239
$1,045,000152 Days on yellowkey MLS ID: A4672440
0 Days Off yellowkey (back on 4/7/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1887 Built: 2003 Tax: $6,901 (2025)Community: GranadaSpa: YesSingle Family
Taxes:$6,901
Remarks: Under contract-accepting backup offers. Spanish Mediterranean home located in Granada subdivision. This courtyard home comes complete with a Casita with great flex space… maybe you need an art studio, separate guest quarters, a caregiver’s suite or a home office. The possibilities are endless. The main house is a two bedroom, two bath residence. The Casita is a one bedroom, one bath space. Both are connected with the central courtyard with potted garden, Mexican tile accents and a spa. The living areas in the home have beautiful vantage points. Kitchen has wood cabinets, stainless appliances, stone counters ,a breakfast bar and direct access to the sitting and dining rooms. The main living room has access to the private back garden with pergola. All bedroom suites are separate private quarters. High ceilings, columns, crown moldings, profile baseboards, led lights, and decorator color palate are some of the features throughout the residence. Home and gardens are meticulously maintained. Granada is minutes to downtown Sarasota, Siesta Key beach, area dining and shopping. Wonderful old oaks trees and sidewalks remain in this Historic Neighborhood.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Tammy Garner (941-374-4161)
2264 FLOYD ST, SARASOTA, FL 34239
$535,000196 Days on yellowkey MLS ID: GC534523
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1564 Built: 1954 Tax: $1,703 (2024)Community: Loma Linda ParkSingle Family
Taxes:$1,703
Remarks: Welcome to 2264 Floyd Street, a charming single-family home located in sunny Sarasota, Florida. This quaint residence was built in 1954 and exudes character and warmth from the moment you arrive. Boasting a spacious finished area of 1,564 square feet, this home offers plenty of room for comfortable living. As you step inside, you are greeted by a cozy living space that flows seamlessly into the dining area, creating the perfect space for entertaining guests or relaxing with loved ones. The kitchen features ample counter and storage space, making meal preparation a breeze. The home also includes one full bathroom, adding convenience for you and your guests. With a lot size of 7,136 square feet, there is plenty of outdoor space to enjoy the beautiful Florida weather. The backyard offers a peaceful retreat, perfect for hosting barbecues or simply unwinding after a long day. The lush landscaping adds to the home's curb appeal and creates a tranquil atmosphere. Located in Sarasota, this home is surrounded by a wealth of amenities and attractions. From world-class beaches to top-rated restaurants and shopping destinations, there is always something to see and do in this vibrant city. Whether you prefer spending your days lounging on the sand or exploring the local art scene, Sarasota has something for everyone. House offers an updated bathroom, new roof and a caged pool area. In the Arlington Park neighborhood where there is a lot of new construction. New homes are $1million and up. Don't miss your chance to own this lovely home on Floyd Street. With its prime location, spacious layout, and charming features, this property is sure to impress. Schedule a showing today and make this house your new home sweet home in Sarasota, Florida.
Listing is courtesy of: COASTAL REAL ESTATE PROFESSIONALS LLC (772-678-6017)
Listing Agent: Zachary Greenberg (561-310-9672)
2600 LOMA LINDA ST, SARASOTA, FL 34239
$375,00033 Days on yellowkey MLS ID: A4686114
REDUCED by $25,000 (6.3%) on 04/06/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1166 Built: 1954 Tax: $4,430 (2025)Community: Arlington ParkSingle Family
Taxes:$4,430
Remarks: Located on a large corner lot in the heart of Arlington Park, this classic Old Florida mid-century home offers an exceptional opportunity in one of Sarasota’s most desirable neighborhoods. Whether you’re looking to renovate and restore its charm or build a custom home, the property provides the ideal setting in a highly sought-after location. Enjoy true walkability with the YMCA just one block away and Arlington Park only two blocks away, featuring walking trails, tennis and pickleball courts, and a heated Olympic-size swimming pool. The neighborhood is known for its mature trees, quiet streets, and close proximity to everything Sarasota has to offer. Just five minutes to Sarasota Memorial Hospital and the vibrant shopping, dining, and cultural attractions of downtown Sarasota, and within easy reach of Sarasota’s world-renowned arts and entertainment scene, including the Van Wezel Performing Arts Hall and The Ringling Museum of Art.Only 15 minutes to the world-famous beaches of Siesta Key, as well as the waterfront dining, boutique shopping, and island lifestyle of St. Armands Circle and Lido Key. This property offers the rare opportunity to enjoy quick access to everyday conveniences, outdoor recreation, Sarasota’s celebrated arts and culture, and the Gulf Coast’s best beaches, all while creating the home or investment vision that fits your needs.
Listing is courtesy of: HARTMAN REAL ESTATE & COMPANY (941-500-4547)
Listing Agent: Zain Hartman (941-735-6415)
3399 ESPANOLA DR, SARASOTA, FL 34239
$465,00014 Days on yellowkey MLS ID: A4688529
0 Days Off yellowkey (back on 4/6/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1622 Built: 1968 Tax: $4,538 (2025)Community: Frst Lakes Country Club EstatesSingle Family
Taxes:$4,538
Remarks: Premier lot… AND it’s fully fenced! This meticulously maintained home in the highly desirable Forest Lakes Country Club community offers the perfect blend of comfort, style, and Florida living. From the moment you walk in, you’ll notice the expansive living spaces and seamless indoor-outdoor flow. NEW HVAC November 2024, HURRICANE-RATED windows and sliders provide peace of mind, while FRESH EXTERIOR PAINT gives the home a crisp, updated feel. The two-panel pocket sliding glass doors open completely, effortlessly connecting the dining and family rooms to the outdoor living space, perfect for entertaining. Step outside to your oversized screened lanai, where you can grill, relax, and host unforgettable gatherings. Enjoy the built-in outdoor kitchen plus plenty of space to lounge in the sun. Wind down your evenings in the lanai all while overlooking the pristine 6th green, your own private oasis right in the backyard. The fully fenced yard offers ample space for pets, play, and large get-togethers, making it as functional as it is beautiful. Inside, you’ll find thoughtful upgrades and modern finishes throughout, including a tile backsplash, updated lighting, and unique concrete countertops. Natural wood accents in the kitchen and primary bathroom add warmth and character, tying everything together beautifully. This home truly has it all. Location, upgrades, and a lifestyle that’s hard to beat. Oh...and only 6.8 miles from the #1 beach in the United States by Tripadvisor (2025) while still being located in the high and dry X-Rated flood-zone.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Michael Pietron (701-213-2740)
1611 HYDE PARK ST, SARASOTA, FL 34239
$3,750,00054 Days on yellowkey MLS ID: A4683619
REDUCED by $449,000 (10.7%) on 04/06/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2545 Built: 1920 Tax: $6,507 (2025)Community: NoneSpa: YesSingle Family
Taxes:$6,507
Remarks: Located in Sarasota’s established West of Trail neighborhood, this gated and fenced 1920 Craftsman residence offers a rare double lot and a guest cottage. Originally constructed in 1920 and comprehensively renovated in 2025 and 2026, the property preserves its architectural character while integrating modern systems, finishes and upgrades including all impact windows and doors. Spanning 3,609 total square feet, the estate is designed for privacy and flexibility. The main residence includes three bedrooms and two and one-half baths. The primary suite is positioned on the main level with direct access to the pool and courtyard, along with a spacious walk-in closet. Large-format porcelain block flooring extends throughout, complemented by updated lighting and professionally curated design elements introduced during the full vintage renovation. The kitchen supports both daily living and entertaining, anchored by a substantial island with quartz countertops, new appliances and a natural gas five-burner range. A dining nook overlooks the pool and courtyard, while adjacent living and lounge areas create seamless gathering spaces. Outdoor living centers around a private courtyard featuring a heated saltwater pool and spa with rock fountain feature, outdoor kitchen, multiple balconies and sitting areas, a sweeping front porch and the landscape lighting is strategically set among the mature Florida landscaping. A custom-built treehouse fort and chicken coop contribute additional character to the grounds. A detached, air-conditioned two-car garage includes a self-contained guest cottage above with one bedroom, office and one bath, with additional covered parking offering flexibility for extended family, guests or potential rental income. Conveniently located near Hillview Street dining and shopping, Morton’s market, the bayfront, Downtown Sarasota and Southside Elementary School, this property combines preserved Craftsman architecture with modern livability in one of Sarasota’s most desirable in-town locations.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Lori Carey, Llc (941-780-3427)
2334 PROSPECT ST, SARASOTA, FL 34239
$355,00023 Days on yellowkey MLS ID: A4686588
5 Days Off yellowkey (back on 4/6/2026)
Bed: 2 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 846 Built: 1952 Tax: $3,003 (2025)Community: Arlington ParkSingle Family
Taxes:$3,003
Remarks: Under contract-accepting backup offers. Positioned along a quiet loop in the heart of Arlington Park, this property presents a rare opportunity for redevelopment in one of Sarasota’s most active and desirable in-town neighborhoods. With no through traffic, Prospect Street offers a more private, residential feel, while still surrounded by a growing mix of new construction and high-end renovations that continue to elevate the area. The existing structure is best suited for removal, allowing for a fresh start and the ability to design a custom home that takes full advantage of the setting. For those with a longer-term approach, the home may also offer the option to renovate and generate interim rental income while plans for future redevelopment take shape. Whether you are a builder seeking your next project or an end user ready to bring a vision to life, this is the kind of opportunity that rarely stays available for long. Buyers are drawn to this area for its unmatched convenience, with easy access to downtown Sarasota, Sarasota Memorial Hospital, Southside Village, and the region’s top dining and cultural destinations, all just minutes away. The nearby Arlington Park and Aquatic Complex adds to the appeal, offering green space, walking trails, and recreational amenities. At the same time, the beaches of Siesta Key are just a short drive away. With no HOA and city rental regulations allowing for short-term leasing, the property also offers flexibility for income-producing use without added restrictions. Secure your place in one of Sarasota’s most dynamic areas and build something that reflects the full potential of this location.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Domanic Calamese (941-914-0038)
2417 PARSON LN, SARASOTA, FL 34239
$395,000120 Days on yellowkey MLS ID: A4675748
2 Days Off yellowkey (back on 4/6/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1316 Built: 1957Monthly Fee: $17 Tax: $5,426 (2025)Community: South GateSingle Family
Taxes:$5,426
Remarks: Don’t miss this adorable South Gate gem! The location could not be more convenient – walk to the Crossings at Siesta Key Mall and less than a mile to the north bridge to Siesta Key itself! For those with school-age children, the close proximity to Brookside Middle School and Southside Elementary zoning are great perks. Completely updated inside with an elegant kitchen (granite, pretty backsplash, stainless appliances), chic wood-look flooring throughout, a charming fireplace, and recently renovated baths, it is move-in ready! Ideally positioned for ultimate convenience to the many amenities of Sarasota, with wonderful possibilities from a full-time or seasonal abode to a prime investment opportunity. The space inside is used really well, with nice spacious bedrooms and a split-bedroom plan, and outside you’ll enjoy a covered screened patio and HUGE fully fenced backyard! There is currently a fun fire pit and open land, so the large yard can be a blank canvas for your outdoor Florida dreams. There is plenty of space for a pool, if that is your desire, or maybe you prefer to plant an edible garden? The choice is yours and this lot can accommodate it all! An oversized 1-car garage with separated extra storage space and laundry completes the package. Easy to show, schedule your visit today!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Allison Werner (941-961-3212)
3052 WEBBER ST, SARASOTA, FL 34239
$535,00031 Days on yellowkey MLS ID: A4685956
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2141 Built: 1964Monthly Fee: $17 Tax: $5,101 (2025)Community: South GateSingle Family
Taxes:$5,101
Remarks: One or more photo(s) has been virtually staged. Step into a piece of Sarasota charm where timeless character meets peace of mind. This lovingly maintained 1964 South Gate gem has been cared for by its original owner and is now ready to welcome its next chapter. Inside, you’ll find a functional split floor plan featuring three bedrooms and two full baths, offering both privacy and flexibility for everyday living. The home feels like a step back in time—in the best way—full of warmth, nostalgia, and the kind of solid construction you just don’t see anymore. Important updates provide confidence where it matters most, including a whole-house re-pipe in 2018, A/C replaced in 2020, and a roof from 2011. Connected to central sewer, this home combines classic appeal with essential modern improvements. Enjoy relaxing mornings or quiet evenings on the back porch, and take advantage of the oversized two-car garage with plenty of room for storage, hobbies, or extra space. Whether you’re looking to preserve its vintage charm or update it to your own style, this South Gate beauty is a rare opportunity to create something truly special in a centrally located, established neighborhood. Homes like this don’t come along often—schedule your private showing today and imagine the possibilities.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Mary Jo Violett (941-928-8474)
3512 CAMINO REAL, SARASOTA, FL 34239
$2,745,000162 Days on yellowkey MLS ID: A4671290
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3810 Built: 2025 Tax: $6,583 (2025)Community: GranadaSingle Family
Taxes:$6,583
Remarks: 3512 Camino Real represents a rare opportunity to acquire a newly constructed luxury residence strategically positioned for high-performing short-term rental income in one of Sarasota’s most supply-constrained residential corridors. Located inside the City of Sarasota and approximately 10 minutes to Siesta Key Beach, Siesta Key Village, and Downtown Sarasota, this property is purpose-built to operate under a weekly rental model that aligns with current city regulations while attracting higher-quality, longer-stay guests. Unlike many coastal investment properties that rely on nightly rental volatility or regulatory gray areas, this home offers a compliant, predictable income profile paired with strong long-term appreciation fundamentals. Completed in 2025 by award-winning Heritage Builders, the British West Indies–inspired residence spans 3,810 square feet on an oversized .27-acre corner double lot, offering 5 bedrooms, 4.5 bathrooms, a dedicated office, a game room, and a 3-car garage. The layout comfortably sleeps up to 12 guests, supporting premium weekly rates and strong demand across multiple seasons. The home’s interior and exterior amenities are intentionally aligned with today’s luxury short-term rental market: a private heated resort-style pool and spa, expansive covered lanai with outdoor kitchen, open-concept living areas, high ceilings, impact-rated windows, concrete block construction, and elevated hurricane standards. These features enhance guest experience while also reducing operational risk, insurance exposure, and long-term maintenance costs—key considerations for investor underwriting. From an operational standpoint, a weekly rental strategy delivers meaningful advantages: fewer guest turnovers, lower housekeeping and wear-and-tear costs, improved booking stability, and reduced party risk. The surrounding Granada neighborhood further strengthens the investment thesis, offering oak-lined sidewalks, walkable parks, proximity to boating access, Southside Village dining, and Downtown Sarasota’s cultural and marina district—all while remaining above the flood zone, a critical differentiator for long-term ownership and asset resilience. Beyond income potential, 3512 Camino Real offers multiple exit strategies. Its new-construction pedigree, desirable residential setting, and luxury finish level support future resale to primary residents, second-home buyers, or continued investor ownership. Limited supply of large, newly built homes with pools inside Sarasota city limits underpins long-term value appreciation and broad buyer appeal across market cycles. A comprehensive Short-Term Rental Investor Report, including projected revenue, operating assumptions, conservative and upside scenarios, and long-term investment analysis, is available upon request and is attached in the MLS for qualified buyers.
Listing is courtesy of: EXP REALTY LLC (800-486-1794)
Listing Agent: Mark Coppens (941-444-0436)
1759 WALDEMERE ST, SARASOTA, FL 34239
$4,449,999193 Days on yellowkey MLS ID: A4666725
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4513 Built: 2025 Tax: $13,348 (2024)Community: Midwood ManorSingle Family
Taxes:$13,348
Remarks: One or more photo(s) has been virtually staged. West of Trail luxury meets modern innovation at 1759 Waldemere Street. This brand-new, custom-built residence embodies timeless design, contemporary craftsmanship, and intentional indoor–outdoor living. Set on a .33-acre lot just steps from Southside Village and Sarasota Memorial, the home delivers sophistication, convenience, and exceptional attention to detail in one of Sarasota’s most sought-after neighborhoods — a rare opportunity in the coveted West of Trail community. Spanning 4,513 square feet, the two-story floor plan features four bedrooms, five baths, an office with private entry, and a media room that opens to a 480-square-foot balcony overlooking the property. Designed for both everyday living and elegant entertaining, the home showcases expansive sliding glass doors that blur the line between indoors and out, opening to a heated saltwater pool, spa, and lush landscaped backyard for year-round enjoyment. The designer kitchen serves as the heart of the home, featuring Sub-Zero and Wolf appliances, custom cabinetry, imported stone, and a hidden butler’s pantry. The first-floor primary suite epitomizes luxury with zero-corner sliders that open directly to the pool and outdoor living area. Inside, a spa-inspired bath includes a freestanding tub, walk-in shower, and a custom built-in walk-in closet. Upstairs, two en suite bedrooms and a second-floor primary suite give privacy for family or guests. A versatile media room and expansive outdoor terrace complete the level, overlooking the serene backyard oasis. Every detail has been thoughtfully curated — from the bespoke, locally handcrafted Sapele wood entry door to hurricane-impact windows and doors, a three-car garage with epoxy flooring, and professional landscaping surrounding the fenced backyard. Ideally located in the highly regarded Southside Elementary School district, near Sarasota Memorial Hospital and the shops and dining of Southside Village, with downtown Sarasota, Siesta Key, Lido Key, and St. Armands Circle just minutes away. This is more than a home — it’s a statement of Sarasota luxury living.
Listing Agent: Rachel Hamrick (941-529-1773)
3013 JENNINGS DR, SARASOTA, FL 34239
$489,000249 Days on yellowkey MLS ID: A4660149
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1364 Built: 1960 Tax: $4,676 (2024)Community: South GateSingle Family
Taxes:$4,676
Remarks: One or more photo(s) has been virtually staged. Priced WELL UNDER APPRAISAL VALUE, this home offers an incredible buyer opportunity in today’s market. This residence, in the highly desirable South Gate neighborhood, comes with up to $8,000 In closing cost credits! Step inside to an inviting open-concept layout where BRAND NEW LVP floors and updated cabinetry create a bright, modern feel. The gourmet kitchen shines with stainless steel appliances, sleek granite countertops, a contrasting tiled backsplash, and rich cabinetry ideal for everyday meals or entertaining friends. The fully fenced backyard provides privacy and plenty of space for outdoor enjoyment. Bring your boat or RV—there’s ample room to store them here! Recent upgrades include LVP Flooring(2026) cabinetry(2026) Primary bathroom(2026) metal roof(2023), AC & Ductwork(2022) Custom closet organizers(2022) plus the home has been fully converted to underground utilities and connected to public water and sewer for peace of mind and lower maintenance. It’s perfect for those seeking room to breathe without the restrictions of an HOA or CDDs. South Gate offers the best of coastal Florida living in a convenient central location. You’re just 4 miles from vibrant downtown Sarasota, 5 miles from world-famous Siesta Key Beach (ranked #1 Beach in the U.S. and #4 in the world), and only 3 miles from Sarasota Memorial Hospital. The Legacy Trail is a quick 2-mile ride away, and excellent schools are nearby. This turnkey, move-in-ready home represents outstanding value. WALK INTO INSTANT EQUITY and schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Tanner Carlson (941-928-9771)
2639 BOUGAINVILLEA ST, SARASOTA, FL 34239
$864,00064 Days on yellowkey MLS ID: A4681333
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2435 Built: 1960Monthly Fee: $17 Tax: $8,234 (2025)Community: South GateSingle Family
Taxes:$8,234
Remarks: Enjoy life to the fullest in this 3 bedroom, 3 bath mid-century modern style ranch home, nestled on a near 1/3 acre lot in the sought-after South Gate neighborhood, offering over 2,400 square feet of architecturally updated and meticulously maintained living space. From the moment you arrive, this private sanctuary impresses with iconic palm trees, a custom circular paver driveway, professionally lit landscaping, and a vivid one-of-a-kind patio with a colorful front entry. Inside, the light and bright open-concept floorplan showcases flawless terrazzo flooring and a striking modern contrasted kitchen with stainless steel appliances and a large island with bar-top seating. The kitchen and living areas flow seamlessly into the family and dining room, providing ample gathering space and an entertainment center ready for modern electronics. French doors lead to an almost 40-foot screened lanai overlooking a professionally manicured, fenced, and irrigated backyard accented with coping. The primary bedroom features a private exterior entrance, space for a desk or seating area, and an en-suite bath with a walk-in closet with built-in shelving and safe, a wall-to-wall glass shower with multiple massage jets and bench seating, and a separate water closet. Two additional contemporary bedrooms and bathrooms are located on the opposite side of the home. The remodeled two-car garage is climate controlled and includes a full laundry room with utility sink. Major upgrades and systems include a standing seam metal roof, hurricane-rated impact windows and garage door, tankless water heater, whole-home generator, updated electrical system with new controls, and a plumbing system rerouted with exterior clean-outs for easy access. The home includes both a 100-gallon and 500-gallon propane tank, with the generator operating from the 500-gallon tank and the water heater capable of running from either tank, all serviced on a regular basis. Indoor comfort is enhanced by a professionally maintained HVAC system with in-duct air purification, including UV lighting and a whole-home purification system. Smart-home features allow remote control of the irrigation system, HVAC, alarm system, front door lock, and security cameras. The driveway has been recently resealed, and exterior security lighting surrounds the home. Optional membership to the South Gate Community Association offers social activities and pool access at the historic community center for a nominal fee. Ideally located just minutes to golf courses, boat clubs, Downtown Sarasota dining, shopping, nightlife, cultural events, and the world-famous beaches of Siesta Key.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Alan Macloughlin (941-780-8628)
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