Location: Sarasota, 34239
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3751 S SCHOOL AVE #11, SARASOTA, FL 34239
$145,00088 Days on yellowkey MLS ID: A4683405
1 Days Off yellowkey (back on 4/23/2026)
REDUCED by $4,900 (3.3%) on 03/31/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 964 Built: 1972 Tax: $1,774 (2025)Community: Sunland AptsCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,774
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Under contract-accepting backup offers. Stunning and move-in ready, this beautifully renovated and fully furnished 2-bedroom, 2-bath condo offers effortless living in an exceptionally convenient central Sarasota location. Perfectly positioned in the heart of the city, you are just minutes from Downtown Sarasota, Sarasota Memorial Hospital, and a straight drive to Siesta Key’s world-famous beaches. Enjoy the rare combination of accessibility and everyday walkability, with popular dining, cafés, and entertainment only a short stroll away. Inside, the condo has been updated to the nines, showcasing a bright, naturally light interior and a complete 2023 renovation including a modern kitchen with quartz countertops and breakfast bar, fully renovated bathrooms, updated flooring throughout, impact (hurricane-rated) windows, and custom window treatments. Offered fully furnished and move-in ready, this residence is ideal for seasonal living, downsizing, or anyone seeking a low-maintenance Sarasota retreat. Ground-floor convenience, a quiet private setting, parking directly outside the unit, and the added benefit of not being located in a flood zone further enhance the appeal. The community pool and laundry facilities are just steps away, adding to the ease of everyday living. Located within a desirable 55+ community, this condo delivers comfort, simplicity, and exceptional lifestyle appeal. Spend your time enjoying Sarasota’s favorite attractions while living in the heart of the city — mornings on Siesta Key’s world-renowned beaches, afternoons exploring local markets and boutiques, and evenings spent dining at the area’s exceptional restaurants. The property can be rented after 1 year of ownership with 4 month lease minimums - no pets allowed. Schedule your tour today!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Ryan Adamson, Pa (941-713-9234)
3368 SHEFFIELD CIR, SARASOTA, FL 34239
$425,000119 Days on yellowkey MLS ID: A4679367
REDUCED by $55,000 (11.5%) on 04/23/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1798 Built: 1969Monthly Fee: $8 Tax: $3,379 (2025)Community: Village Green Club EstatesSingle Family
Taxes:$3,379
Elementary School: Wilkinson Elementary
Remarks: Enjoy the best of Sarasota living in this centrally located, fully fenced home with impact windows, circular driveway, with an amazing private outdoor living space that is minutes from shopping, dining, and a short drive to the sugar-sand beaches of Siesta Key. Thoughtfully updated and designed for comfortable everyday living, this home offers a flexible floor plan and inviting spaces both indoors and out. Inside, the light and bright interior features a crisp, clean feel and a desirable split-bedroom, open floor plan. Modern light wood-look laminate flooring flows throughout the home. The entryway includes a convenient coat closet and the open dining and living room combination offers flexibility for entertaining and everyday living. The interior flows seamlessly from the front of the home through the family room and out to the enclosed lanai. The kitchen showcases white shaker cabinets, granite countertops, a glass subway tile backsplash, and stainless steel appliances making it both stylish and functional. The spacious primary suite features tall windows, a large walk-in closet, and an en suite bathroom that offers a shower/tub combo and a thoughtful layout with the toilet and shower separated from the vanity. The guest bedroom is generously sized, and the updated guest bathroom features tile flooring, a large stone shower with glass doors, and granite countertops. Enjoy Florida living year-round with an enclosed, multi-use lanai featuring tile flooring and expansive glass windows that add valuable living space, along with an additional screened rear patio perfect for a more open-air outdoor experience. The vinyl-fenced backyard with lush tropical landscaping completes the home’s rear outdoor oasis. With a great location and stylish updates throughout, this home is ready to be enjoyed. Come see it, feel the charm, and make it your own!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Karie Backman (941-404-8389)
2089 ARLINGTON ST, SARASOTA, FL 34239
$2,961,700109 Days on yellowkey MLS ID: TB8471775
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4231 Built: 2026 Tax: $6,925 (2025)Community: La Linda TerraceSpa: YesSingle Family
Taxes:$6,925
Elementary School: None
High School: None
Middle School: None
Remarks: 2089 Arlington Street, where architecture meets light, space, and coastal elegance, this newly constructed contemporary residence offers 4,231 square feet of living space and 5,284 total square feet, thoughtfully designed with architectural precision and warm minimalism. Completed in January 2026, this striking two-story home sits on a rare double corner lot and features 5 bedrooms and 6 bathrooms, delivering both scale and sophistication. The open-concept interior is defined by dramatic 22-foot ceilings, expansive custom windows and doors, and an abundance of natural light throughout. The main level is anchored by a statement chef’s kitchen imported from Italy, showcasing custom cabinetry, luxury built-in appliances, a Sub-Zero refrigerator, premium hardware, and top-quality London Fog granite countertops. A concealed secondary kitchen provides additional functionality and discretion, ideal for entertaining and catered events. The primary suite is conveniently located on the ground floor, offering a private retreat with serene views and a spa-inspired bath. Additional bedrooms are generously sized, each with access to a full bathroom. A custom glass wine room adds a refined architectural focal point, while a loft-style family/media lounge on the second level overlooks the main living area, enhancing the home’s open, airy feel. Designed for seamless indoor–outdoor living, oversized sliding doors open to a private resort-style setting with a custom pool and spa, covered terrace, and enhanced landscaping. Architectural exterior lighting highlights the home’s clean lines and modern façade after sunset. Quality and performance are paramount: both levels are constructed of solid concrete block, and three independent HVAC systems serve the ground floor, primary suite, and second floor for optimal comfort and efficiency. Additional features include a private elevator, and all custom-made windows, doors, and cabinetry throughout—evidence of meticulous attention to detail in every finish. Ideally located for effortless travel and coastal lifestyle enjoyment, this home is approximately 12–15 minutes from Sarasota–Bradenton International Airport, about 1 hour 10 minutes from Tampa International Airport, 10–15 minutes to Lido Key, and about 15 minutes to Siesta Key, world-renowned for powder-white sand and Gulf sunsets. Situated outside of a flood zone, this exceptional residence presents a rare opportunity to own a custom-built contemporary home where design, craftsmanship, location, and lifestyle converge.
Listing is courtesy of: COMPASS FLORIDA, LLC (305-851-2820)
Listing Agent: Estela Ziu (813-858-6267)
2613 TEMPLE ST, SARASOTA, FL 34239
$1,199,000179 Days on yellowkey MLS ID: A4673045
0 Days Off yellowkey (back on 5/10/2026)
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3308 Built: 1997 Tax: $5,102 (2025)Community: Highland Park 2Spa: NoSingle Family
Taxes:$5,102
Elementary School: Alta Vista Elementary
Remarks: Under contract-accepting backup offers. PRICED TO SELL AT $1,199,000 , this is your chance to own a home with incredible value. A NEW METAL ROOF IS SCHEDULED FOR APRIL -giving buyers instant peace of mind and long-term savings from day one. A rare offering with architectural character and privacy, this property presents exceptional value for buyers seeking a truly special one-of-a-kind retreat. Welcome to Storybook — a treetop sanctuary where architecture, nature, and artistry meet! Tucked away in Arlington park at the end of a private canopied road and surrounded by native Florida landscaping and protected wetlands, this extraordinary 3-bedroom, 4-bathroom residence with a custom library/den feels like a hidden world all its own. Designed by renowned Sarasota architect Richard G. Allen, known for his sustainable and expressive style, Storybook lives up to its name — enchanting, serene, and timeless. Soaring ceilings, exposed wood beams, and maple floors create a warm, open-concept living space that flows effortlessly to the outdoors. Clerestory windows invite natural light, while the wraparound porch and treetop pool immerse you in the surrounding canopy. A spiral staircase ascends to a light filled loft offering both inspiration and a tranquil retreat above it all. This home's heart resides in a custom library/den, a quiet sanctuary where books, ideas, and conversation gather. Beyond the cozy den lies an en suite bedroom, a serene space inspired by Zen simplicity. Sliding glass doors open to the wraparound patio, a haven for morning coffee and quiet reflection. On the same floor, a second primary suite welcomes you through an intricately hand carved door. Inside, an expansive bedroom and private sitting area rests quietly among the treetops, wrapped in peaceful seclusion. The ground floor includes a private guest suite and entrance, spacious laundry room, ample storage, oversized two-car garage ,and EV charging station. From the hand-carved Tibetan gates to the tranquil pond and water feature, every detail of Storybook reflects a reverence for Sarasota’s natural beauty and a deep sense of peace and privacy. This is more than a home — it’s a place to breathe, reflect, and feel fully connected to the world around you.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Dianne Anderson (941-350-3513)
2100 MCCLELLAN PKWY, SARASOTA, FL 34239
$6,000,00063 Days on yellowkey MLS ID: A4685416
Bed: 5 Bath: 8.0 Gar: 3 Liv Area Sq Ft: 4765 Built: 2026 Tax: $14,834 (2025)Community: Mcclellan Park ResubSpa: YesSingle Family
Taxes:$14,834
Remarks: Pre-Construction. To be built. Construction in progress, and opportunity for customizations. Situated West of the Trail, this exceptional estate represents the pinnacle of luxury living in Sarasota. Developed by Pham Development, this residence is a masterpiece of innovative, forward-thinking design and flawless craftsmanship. This home is 4,765 square feet, with 5 bedrooms, 7 baths and 2 half baths. Inside, you'll discover an open floor plan that harmoniously blends expansive spaces with comfortable, luxurious living. The soaring, 18-foot vaulted ceilings and seamless transitions between the grand indoor living areas, multiple patios, wrap-around balconies, and lush outdoor grounds make this home ideal for intimate gatherings and larger events alike. The well-appointed kitchen features an open-concept layout, highlighted by a stunning quartz island with waterfall edges, under elegant pendant lighting. Custom cabinetry in a sleek, glossy finish complements the state-of-the-art stainless-steel appliances, which include a professional-grade gas range, double ovens, and a built-in espresso machine. A discreet entry leads to a spacious butler’s pantry, offering additional storage, a secondary sink, and a prep area - perfect for hosting large gatherings or keeping the main kitchen organized. The pantry also mirrors the kitchen’s custom cabinetry and countertops for a seamless design. Adjacent to the dining area, a glass-enclosed, temperature-controlled wine room adds both style and function, and is sure to beautifully showcase your wine collection with custom shelving and ambient lighting. The expansive primary bedroom features 14-foot vaulted ceilings and large windows that fill the room with natural light. Soft, neutral tones create a serene environment, while the en-suite bathroom offers a spa-like retreat with a freestanding soaking tub positioned beneath a large window. Dual sinks with quartz countertops and sleek fixtures provide ample space, and the frameless glass walk-in shower features multiple shower heads and exquisite tile work. For entertainment, the theater room is a dream come true, offering tiered seating with oversized leather recliners - each equipped with cup holders and personal charging stations. The ultra-high-definition projection screen spans an entire wall, ensuring an immersive viewing experience. Outside, the resort-style pool is the centerpiece of the backyard, complete with a built-in spa, waterfall, and ambient lighting. A natural stone deck, covered lanai dining area, and a fully equipped outdoor kitchen and bar provide the perfect setting for outdoor living. A cozy fire pit with seating offers a perfect gathering spot for evenings, while the lush landscaping - featuring vibrant flower beds, mature trees, and decorative water features - creates a tranquil and picturesque setting. This outdoor space seamlessly combines comfort, style, and functionality for an exceptional living experience. Positioned on a grand parcel of approximately 20,505 square feet, this home offers privacy and tranquility amidst beautifully landscaped grounds. Whether you’re seeking the excitement of downtown Sarasota or the natural beauty of the Gulf, experience the perfect blend of luxury, comfort, and convenience in this exceptional home in a fabulous location.
Listing is courtesy of: THE STUTZMAN REALTY GROUP, LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
2639 BOUGAINVILLEA ST, SARASOTA, FL 34239
$844,99998 Days on yellowkey MLS ID: A4681333
REDUCED by $19,001 (2.2%) on 04/23/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2435 Built: 1960Monthly Fee: $17 Tax: $8,234 (2025)Community: South GateSpa: NoSingle 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)
2833 SUNNYSIDE ST, SARASOTA, FL 34239
$549,90014 Days on yellowkey MLS ID: N6143993
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1263 Built: 1959Monthly Fee: $17 Tax: $4,839 (2024)Community: South GateSpa: NoSingle Family
Taxes:$4,839
Tax Year: 2024
Middle School: Sarasota Middle
Remarks: Welcome to 2833 Sunnyside Street, a beautifully renovated South Gate residence where timeless Sarasota charm meets modern comfort and effortless Florida living. Perfectly positioned in one of Sarasota’s most desirable and centrally located neighborhoods, this move-in-ready home offers 3BR, 2BA and a versatile sunroom flex space ideal for a home office, playroom, gym, creative studio, or additional lounge area. From the moment you arrive, the home’s inviting curb appeal, updated landscaping, and thoughtfully designed finishes create an immediate sense of warmth and sophistication. Inside, you’ll find a bright and airy open-concept layout featuring stunning restored original terrazzo floors throughout, stylish upgraded lighting, and a seamless flow designed for both everyday living and entertaining. At the heart of the home is a completely renovated designer kitchen showcasing premium Bosch appliances including a Benchmark Series induction range, 800 Series refrigerator and dishwasher, a Brizo faucet, Franke under mount sink, and beautiful Cambria quartz countertops. Expansive windows fill the home with natural light, while the spacious primary suite provides a peaceful retreat complemented by beautifully updated bathrooms and thoughtful designer finishes throughout. This home has been extensively upgraded for both style and peace of mind, including a newer shingle roof (2021), updated HVAC systems (2018/2019), PVC plumbing, new water heater, and new electrical panels with increased 200-amp service. Additional improvements include freshly painted interior walls, ceilings, doors, closets, and baseboards, restored terrazzo flooring, new Toto toilets, upgraded lighting, all new blinds and curtains and ceiling fans installed in the sunroom, living room and secondary bedrooms. The oversized two-car garage features a sleek epoxy floor, while underground utilities enhance the neighborhood’s clean and polished appearance. Situated on nearly 1/4 acre, the oversized fully fenced backyard with white vinyl fencing offers exceptional privacy and endless possibilities with ample room for pets, play, gardening, or even the pool of your dreams. The covered and screened lanai creates the perfect setting to enjoy morning coffee, outdoor dining, or relaxing evenings year-round while embracing the Florida lifestyle. Adding even more appeal, this home is located in Flood Zone X with no history of water intrusion and features an optional HOA giving homeowners added flexibility without the burden of mandatory fees or restrictions. Ideally located just minutes from Siesta Key Beach, Downtown Sarasota, Southside Village, Arlington Park, Sarasota Memorial Hospital, and the vibrant shopping and dining destinations along Hillview Street, this exceptional property offers the perfect blend of location, lifestyle, and modern upgrades. Families will also appreciate the highly sought-after school zoning for Southside Elementary, Sarasota Middle School, and Sarasota High School. Rarely does a home in South Gate combine this level of renovation, functionality, outdoor space, and prime Sarasota location. 2833 Sunnyside Street is truly a must-see opportunity.
Listing Agent: Erica Giesler (813-352-4008)
1655 SOUTH DR, SARASOTA, FL 34239
$5,900,00082 Days on yellowkey MLS ID: A4684423
Bed: 5 Bath: 7.0 Gar: 3 Liv Area Sq Ft: 6355 Built: 2011Monthly Fee: $27 Tax: $34,625 (2025)Community: Cherokee ParkSpa: YesSingle Family
Taxes:$34,625
Remarks: One or more photo(s) has been virtually staged. In Sarasota's desired West of Trail enclave of Cherokee Park, 1655 South Drive, masterfully designed three-story estate where thoughtful architecture meets effortless luxury. Positioned on a homesite that is not in a Special Flood Hazard Area and enhanced with full home hurricane-impact glass and a whole-home generator, this residence offers the rare combination of refinement and peace of mind. Spanning 6,355+ square feet, the home features five bedrooms, five full baths and four half baths, with a layout tailored for grand entertaining and everyday ease. A rear three-car garage, accessed discreetly from South Lodge Drive, preserves the home's striking street presence. Inside, the main level unfolds into a wide-open living experience with a great room with wet bar, formal dining, and a showpiece chef's kitchen outfitted with Wolf dual-oven six-burner range, dual side by side 36” Sub-Zero Over-and-Under Refrigerator/Freezers, a Wolf microwave drawer, a Wolf warming drawer, and built-in Miele espresso machine. The first-floor primary suite is a private retreat, complete with an in-home gym, a spa-inspired bath and dual custom-fitted closets. A beautifully appointed guest suite (fifth bedroom) with en-suite bath also anchors the main level. Access to the upper floors is seamless via a dramatic staircase with custom wrought-iron railings or the private elevator. Upstairs, three additional en-suite bedrooms include custom walk-in closets, one thoughtfully designed with built-in bunk beds, plus a bonus club room with built-in desks and additional laundry for added convenience. Outdoors, the property transforms into a walled and gated resort-style oasis featuring a gas-heated saltwater pool with sun shelf and spa, and an artificial turf lounge/play area. A screened entertainment lounge with a convenient half pool bath connects to a full outdoor kitchen with sink, TV and gas grill, all complemented by a pergola and a mosquito misting system, ideal for Sarasota's seasons. Above the garage, a spectacular casita-style retreat, accessible by the home’s second private interior elevator or exterior spiral staircase, elevates entertaining to an entirely new level with a 2,000-bottle refrigerated wine room, a fully equipped wet bar, mini- fridge, clear ice maker, and dishwasher. Go onto the covered terrace with a gas fireplace, then unwind on the third floor in the private, pool-like infinity-edge spa, an experience that feels equal parts boutique resort and private club. Ideally in walking distance to A-rated Southside Elementary School, Southside Village, Sarasota Memorial Hospital, downtown Sarasota and short drive to the world-famous sands of Siesta Key Beach, this is a rare opportunity to own a bespoke residence in one of Sarasota's treasured neighborhoods.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Katy Mcbrayer (941-400-2406)
1607 FLOWER DR, SARASOTA, FL 34239
$4,290,000347 Days on yellowkey MLS ID: A4653737
Bed: 5 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 4769 Built: 2024 Tax: $16,090 (2024)Community: Harbor Acres Sec 2Spa: YesSingle Family
Taxes:$16,090
Remarks: One or more photo(s) has been virtually staged. LOWEST PRICED NEW CONSTRUCTION WEST OF TRAIL HOSPITAL/SOUTHSIDE VILLAGE AREA! Truly a Coastal Classic Modern Masterpiece Located in One of the MOST Sought After Neighborhoods West of the Trail in Sarasota! This Gorgeous HARBOR ACRES Home is NOT your Typical Very Traditional Boring Florida Home! This Home was Built for the Discerning Buyer who Appreciates Modern Art and Design! Every Room is Unique and Designed with Attention to Detail and Gracefully Incorporates the Outside Indoors via Walls with Large Picture Windows. This Amazing Property Features: A MAIN HOUSE w/5 Bedrooms, 5.5 Baths, 2 Master Suites (Up & Down) both w/Zen-like 5-Piece Master Baths w/Whirlpool Soaking Tubs and Separate Showers; Fabulous Great Room w/Soaring Ceilings, Wall Fireplace and Sliders Looking Out to the Aqua Pool and Spa and Tropical Landscape; Extra Flex Room off Kitchen w/Built in Art Niche makes a Perfect Dining Room, Den/Office w/Built-ins, Fabulous Kitchen w/Separate Refrigerator, Freezer & Wine Refrigerator, Luxury Dacor Appliances, Quartz Counters, Designer Kitchen Cabinetry, Pantry, Eating Bar; Media Bonus Room w/Balcony, Laundry Room w/Storage, Open Glass Staircase to Upstairs, Elevator Shaft to All Floors, Porcelain Tile and Elegant Lighting Fixtures throughout, Bosch AC Units, 2 Balconies Upstairs, En-Suite Bedrooms, Powder Room w/Glass Art Sink, Impact Windows and Sliders w/Low E Glass, Oversized 2 Car Garage and an Oversized 1 Car Garage w/Electric Charging Stations, Smart Home w/Fully Integrated Wifi System, Covered Lanai w/Fully Equipped Out Door Kitchen and Fire Pit. A Detached CASITA GUEST HOUSE w/Separate Entrance, Full Bath, Kitchenette and One Bedroom overlooking the Pool Court Yard, Perfect for a Nanny, House Keeper, Teen, MIL or Pool Party Room. The Outdoor Features: Gorgeous 35 Foot Saltwater Pool w/Waterfall, Huge Sun Shelf and Hot Tub Spa; Lush Tropical Landscaping, Tiered Flower Planters, Low Maintenance Yard, Irrigation, Circular Driveway and Privacy Wall. Home was Built nearly 2 FT above the Flood Zone and does NOT Require Flood Insurance. This Never Before Been Lived in Home is Ready and Waiting for It's New Owner! Located just Minutes to Sarasota Memorial Hospital and Medical Center, Morton's Market, Downtown Sarasota, Shopping, Dining, St Armand's and the Best Beaches!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Anne Thomas, Pa (941-993-7700)
2458 WALDEMERE ST, SARASOTA, FL 34239
$479,50024 Days on yellowkey MLS ID: N6144122
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1648 Built: 1952 Tax: $7,101 (2026)Community: SingletarysSpa: YesSingle Family
Taxes:$7,101
Tax Year: 2026
Remarks: Experience the perfect harmony of modern upgrades and versatile living in this beautifully refreshed residence situated in the heart of one of Sarasota’s most established neighborhoods. This meticulously maintained home welcomes you with durable tile flooring throughout the main living areas, complemented by stylish vinyl flooring installed in the primary suite in 2021 and a crisp, neutral paint palette that enhances the natural light. The thoughtfully designed floor plan includes a true mother-in-law suite featuring its own private entrance, providing an ideal sanctuary for multi-generational living or a secluded home office. This secondary wing opens to its own covered and screened lanai, offering a peaceful retreat separate from the main household. The home has been extensively modernized for peace of mind, featuring a new roof installed in 2022, updated windows, updated plumbing, and a contemporary electrical panel. Climate control is effortless with two dedicated A/C systems, including a brand-new rear unit installed in 2024, along with a new water heater added the same year. The heart of the home showcases a kitchen equipped with a new refrigerator and dishwasher, while the living area centers around a cozy fireplace with elegant new tile work. Luxury extends to the bathrooms, where the primary ensuite features a refreshed walk-in shower and a tub recoated in 2025 that includes a transferable warranty. Elegant French doors lead you to a freshly re-tiled screened lanai, perfect for enjoying the Florida lifestyle within the privacy of a fully enclosed backyard, secured by a new fence and gate installed in 2025. Located in a premier school district including Southside Elementary, Brookside Middle, and Sarasota High School, this property is just minutes from the cultural heartbeat of Downtown Sarasota, the luxury boutiques of St. Armands Circle, and the bright sands of Siesta Key Beach. With nearby access to Sarasota Memorial Hospital and the Arlington Park aquatic center, this move-in-ready estate offers a rare combination of structural integrity and an unbeatable location.
Listing Agent: Patrick Brogley (941-361-9031)
2205 FLOYD ST, SARASOTA, FL 34239
$622,50021 Days on yellowkey MLS ID: A4691727
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1954 Tax: $7,102 (2025)Community: Arlington ParkSingle Family
Taxes:$7,102
Remarks: Welcome to this beautifully reimagined residence in the highly sought-after Arlington Park neighborhood, where modern updates meet a peaceful, tucked-away setting. Completely renovated from top to bottom in December 2023, this home showcases meticulous attention to detail throughout. Perfectly positioned on a corner lot along a quiet dead-end street, the home enjoys a unique sense of privacy, with mature trees, lush landscaping, and a shaded backdrop that enhances the serene setting. Enter through the front door into a light-filled interior, where thoughtful design and quality craftsmanship are immediately apparent. Rich hickory hardwood flooring flows throughout, complemented by a fresh, neutral palette, updated trim, and refined finishes that create a cohesive and inviting atmosphere. The main living space unfolds with effortless flow, offering a bright and welcoming environment ideal for both everyday living and entertaining. The large dining/breakfast area features sliding glass doors which draw the eye outward and open to a newer constructed deck, seamlessly blending indoor and outdoor living. The updated kitchen is both stylish and functional, featuring solid wood cabinetry, sleek quartz countertops, updated stainless appliances, and a tasteful backsplash, creating a space that is as practical as it is visually appealing. The primary bedroom offers a comfortable retreat, while the bathrooms have been completely transformed with designer selections. The main bath showcases a double vanity, elegant finishes, and a beautiful Kohler cast iron tub paired with Moen fixtures. The guest bath features a new glass shower enclosure, continuing the home’s elevated aesthetic. 2 additional bedrooms provide flexibility for family, guests, or a home office, each thoughtfully finished with updated flooring, lighting, and fixtures. A brand-new front-load LG washer and dryer adds everyday convenience. Step outside to a private, fenced backyard framed by mature areca palms and low-maintenance rock landscaping, creating a tranquil outdoor setting. A double-gated fence offers valuable space for storing a boat or small RV, while the newly coated carport enhances both function and presentation. Improvements in 2023 include all new electrical wiring brought up to current Florida Building Code, new water supply lines, replacement of cast iron drain lines with PVC, new insulation and drywall including ceilings, updated lighting and fixtures, a new HVAC system, water heater, and fresh exterior paint—delivering peace of mind and true move-in readiness. Ideally located just moments from Arlington Park’s walking trails, dog park, and recreational amenities, and only minutes to Sarasota Memorial Hospital, downtown Sarasota, and the world-renowned beaches of Siesta Key and Lido Key, this residence offers an exceptional combination of location, lifestyle, and investment potential with flexible minimum lease options. Schedule your showing today!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lenore Treiman (941-356-9642)
3751 S SCHOOL AVE #29, SARASOTA, FL 34239
$124,999203 Days on yellowkey MLS ID: A4670178
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 964 Built: 1972 Tax: $1,874 (2025)Community: Sunland AptsSpa: NoCondo
Taxes:$1,874
Remarks: Recently updated with a new roof in August and no assessments! Prime location! Welcome to Sunland Garden Apartments, a charming 55+ condo community nestled behind The Crossings at Siesta Key Mall, which is currently undergoing redevelopment into a vibrant mixed-use development featuring retail shops, restaurants, and offices. Notably, Connors Steak & Seafood and Cinebistro are expected to remain! Ideally situated in central Sarasota, just a short drive to our stunning beaches. This third-floor unit offers two bedrooms with en-suite baths, walk-in closets, and the largest screened porch in the community equipped with hurricane roll shutters. Enjoy peaceful courtyard views, along with access to the community pool, BBQ area, and shuffleboard court. Being on the top floor means there are no neighbors above. Both bedrooms and the living room have sliding glass door access to the spacious, covered porch. The unit features a new front storm door, replaced A/C and hot water heater (both in 2019) with biannual maintenance, and a brand-new garbage disposal. The laundry room and a large storage cage are just steps from your front door, near the elevator and stairs for easy access. Your assigned parking spot and adjacent guest parking are conveniently located right in front of the unit. Enjoy proximity to Sarasota’s vibrant downtown scene, less than 3 miles away, with numerous entertainment venues, dining, theaters, and art galleries. Numerous parks and golf courses are also just minutes from the community. This property is perfect as a part-time escape or full-time residence!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Angie Unzicker (941-809-9119)
1761 SIESTA DR & 1760 WISCONSIN LN, SARASOTA, FL 34239
$2,400,00049 Days on yellowkey MLS ID: A4688714
0 Days Off yellowkey (back on 5/6/2026)
Bed: 10 Bath: 0.0 Liv Area Sq Ft: 4435 Built: 1949 Tax: $9,643 (2025)Community: BayviewApartment
Taxes:$9,643
Remarks: Under contract-accepting backup offers. 7 Rentable Units | 10 Bed, 8 Bath Income Property – Prime Siesta Key Location! Exceptional opportunity to own a fully leased multifamily property just minutes from world-famous Siesta Key Beach. Located on Siesta Drive—the gateway to Siesta Key—this offering includes two adjacent triplexes on two separate lots, with potential to expand to 8 units. The property features a versatile mix of 1BR, 2BR, 3BR, and studio layouts, ideal for maximizing rental income. Zoned for weekly rentals (7-day minimum) within city limits, this property offers strong income potential with a blend of long-term tenants and proven short-term rental performance (Airbnb 5-star host/seasonal). Recent upgrades include newer roofs (2016–2017), new siding, updated A/C units, hot water heaters (2021+), appliances, exterior plumbing, fencing, and security lighting/cameras. Professionally landscaped grounds enhance curb appeal. On-site laundry with the ability to add laundry to every unit. Tenants pay utilities with 7 separate water and electric meters. Situated just blocks from the North Bridge and within walking distance to shopping, dining, and everyday conveniences. Located in an X flood zone – NO flood insurance required, and Level D evacuation zone. Ample parking for up to 17 vehicles, plus space for boats, kayaks, and recreational toys. Buy one or both – must be sold simultaneously: 1761 Siesta Dr & 1760 Wisconsin Ln – a rare high-income investment package on Siesta Key. Strong financials: ~5.19% cap rate, under $20K in annual expenses, and projected income of $175K+ with upside potential. Do not disturb tenants. Showings by appointment only; listing agent must accompany all showings.
Listing Agent: Danielle Dietrich, Pa (603-767-9166)
1347 HARBOR DR, SARASOTA, FL 34239
$4,000,000116 Days on yellowkey MLS ID: A4679697
REDUCED by $300,000 (7.0%) on 05/07/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4069 Built: 2014Monthly Fee: $13 Tax: $57,247 (2025)Community: Harbor AcresSpa: YesSingle Family
Taxes:$57,247
Remarks: Exceptional Harbor Acres modern residence offering 5 bedrooms, including a sunroom converted by the owners into a true 5th bedroom (closet and A/C). Warm contemporary design with seamless indoor-outdoor living. Located in Harbor Acres, one of Sarasota’s most coveted neighborhoods, this exceptional modern residence delivers a rare blend of warm contemporary design, luxury finishes, and seamless indoor-outdoor living. Perfectly scaled for the neighborhood, the open floor plan is flooded with natural light and effortlessly blurs the line between inside and out. The great room features 8-ft pocketing sliders opening to the covered lanai, anchored by a gas fireplace with illuminated floating shelves. The chef’s kitchen is a showpiece with top-of-the-line Miele appliances, solid wood cabinetry, an expansive quartz island, LED lighting, and a butler’s pantry for effortless entertaining. A separate dining room with picturesque windows offers an inviting setting for intimate gatherings, while the adjoining family room provides a relaxed space to unwind. The first-floor primary suite is a serene retreat with walls of windows overlooking lush tropical foliage and a spa-inspired bath featuring a soaking tub and glass shower. A dedicated office/flex room is conveniently located on the main level. Owners thoughtfully converted the sunroom into a 5th bedroom, offering added flexibility for guests or multigenerational living. Sleek open-riser stairs lead upstairs to two en-suite bedrooms providing privacy and comfort.
Listing is courtesy of: MICHAELA DAMM & PARTNERS (941-726-1808)
Listing Agent: Miska Damm (941-726-1808)
1934 DATURA ST, SARASOTA, FL 34239
$1,600,000109 Days on yellowkey MLS ID: A4680304
0 Days Off yellowkey (back on 5/7/2026)
REDUCED by $25,000 (1.5%) on 04/22/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3091 Built: 2002 Tax: $9,130 (2025)Community: Desota ParkSingle Family
Taxes:$9,130
Remarks: A striking residence on one of Sarasota's treasured streets West of Trail, crowned with a NEW BARREL STYLE METAL ROOF, showcasing a raised front porch and grand double-door entry, all enveloped by a lush, resort-style tropical garden. This expansive home just freshly painted and professionally staged, offers four generously sized bedrooms, one boasting it's own large patio in the treetops. With over 3,000 square feet of thoughtfully designed living space, the home blends timeless elegance with comfort, creating an inviting setting for upscale entertaining and everyday living. Be welcomed by a grand two-story vaulted living and dining space, highlighted by an elegant curved staircase and open catwalk above. The spacious chef’s kitchen features a center island and breakfast bar, flowing seamlessly into the family room and through expansive sliding glass doors to a screened patio that evokes the feel of a private tropical paradise. The primary suite is conveniently on the main level, offering soaring ceilings and direct access to the patio. It includes a custom walk-in closet and a spa-inspired bath with dual vanities, a garden tub and a separate shower. Recent updates include NEW CARPETING IN ALL BEDROOMS, NEWER DUAL ZONED AIR CONDINTIONG SYSTEMS for optimal comfort, a NEW HOT WATER TANK and a COMPLETE WHOLE HOUSE RE-PLUMB, offering peace of mind and modern efficiency. ROOM FOR A POOL. Just steps away from Morton's Market, Veronica's, and other neighborhood favorites. Located in the highly regarded Southside Elementary School district, the home offers the very best of the West of Trail lifestyle, walkable to restaurants, boutiques shops, Sarasota Memorial Hospital, with easy access to downtown Sarasota and our world-famous beaches.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-907-9541)
Listing Agent: Christine Mazur (941-374-4015)
2907 MARSHALL DR, SARASOTA, FL 34239
$599,999210 Days on yellowkey MLS ID: A4669618
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1138 Built: 1954 Tax: $6,643 (2025)Community: Orange ParkSpa: YesSingle Family
Taxes:$6,643
Remarks: Investor Alert! Rare opportunity to own a turnkey income-producing property in a prime location! This fully furnished gem features a brand-new pool, all-new impact windows, and a strong rental history with future bookings already in place, cash flow from day one! Don’t miss your chance to add this high-performing asset to your portfolio. Schedule your showing today, opportunities like this don’t last!
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Inbal August (917-957-8111)
1760 WISCONSIN LN, SARASOTA, FL 34239
$1,300,00049 Days on yellowkey MLS ID: A4688606
Bed: 5 Bath: 0.0 Liv Area Sq Ft: 2175 Built: 1948 Tax: $4,763 (2025)Community: BayviewApartment
Taxes:$4,763
Remarks: Under contract-accepting backup offers. Siesta Key Triplex – Weekly Rental Zoned Investment Opportunity Concrete triplex in city limits featuring one 3BR/1BA unit with attached 1BR/1BA studio and two additional 1BR/1BA units. ALL units are tenant-occupied with immediate income potential; historical annual income reported at $80K–$100K. Zoned for weekly rentals in Siesta Key City Limits...allow short- or long-term rental flexibility. Property includes four electric and four water meters, with tenants paying utilities. Expenses are kept low and are primarily limited to taxes, insurance, and landscaping. Recent updates include A/C systems, water heaters, appliances, exterior lighting, security cameras, and landscaping. Features shared on-site laundry plus private laundry in the larger unit. Concrete construction makes this the perfect investment property close to the beach and in Evacuation Zone D. No flood insurance required! Prime location near Siesta Key Beach with easy access to shopping, dining, and public transportation. Approximately two blocks to the North Bridge. Add 1761 Siesta Dr to increase your income potential and begin your Siesta Key Portfolio or scale to a 7+ unit portfolio with a potential six-figure+ income gain. Why buy just one when you can buy both! Strong in-place income makes this a rare Siesta Key investment. Intended to be sold together. Do not disturb tenants. Showings by appointment only; listing agent must accompany all showings.
2421 PROSPECT ST, SARASOTA, FL 34239
$629,500123 Days on yellowkey MLS ID: A4677367
REDUCED by $16,400 (2.5%) on 04/30/2026
Bed: 3 Bath: 1.5 Liv Area Sq Ft: 972 Built: 1956 Tax: $4,592 (2025)Community: Arlington ParkSingle Family
Taxes:$4,592
Remarks: Under contract-accepting backup offers. Welcome to 2421 Prospect Street in Arlington Park’s Tightly Held RUSTIC LODGE…This Elegantly Refined Florida Mid-Century Retreat is Rooted in Sarasota’s Golden Era…the 1950s Marked a Time When Homes Were Designed & Built with Longevity & Craftsmanship—and 2421 Beautifully Honors That Legacy…Approached Not as a Renovation but as a Custom Crafted Rebuild…a Design-Conscious Builder Preserved the Home’s Original Vision While Elevating It for Today’s Style, Comfort & Quality…the Integrity, Proportions, and Character Remain Intact, Enhanced by Refined Finishes, Integrated Systems, Forward-Thinking Infrastructure, and City of Sarasota Code Improvements…Sleek, Clean & Effortlessly Cool—As Though the 1950s Walked Into 2026 with Style…Expansive New PGT Impact Windows, Sliders & Doors Bathe the Home in Natural Light While Preserving Tranquility…Every Detail Has Been Carefully Considered, Including All New Plumbing with Cast Iron Replacement Under the Slab, All New Electrical, HVAC Ductwork, Engineered Structural Enhancements for an Open Floorplan, Insulated Interior Walls, Blown Attic Insulation, Tankless Water Heater, White Oak Style Plank Flooring, Frameless Glass Shower Doors, Custom Walk-In Closets, and Soft-Close Cabinetry Throughout…Curated Quartz Countertops Extend Across the Gourmet Kitchen, Catering Pantry, Dry Bar, and Bathrooms…Recently Enhanced with a Brand-New Stainless Steel LG Dishwasher & GE Profile Refrigerator…Glass Tile Backsplashes, a Substantial Kitchen Island with Tile Accent Lighting, and a Vented Range Hood Complete the Kitchen Experience…Discreetly Integrated Throughout is a Fully Automated Smart Home System Offering Remote Entry Keypads, Wireless Alarm, Ring Cameras, Motion Detectors, Panic Buttons, In-Wall Safe, Remote-Control Ceiling Fans, USB-C Outlets, Nest Thermostat, and Digitally Controlled Irrigation—Allowing the Home to Be Fully Automated or Enjoyed Traditionally…A Fully Screened Lanai and Carport, Both with Custom Tongue & Groove Ceilings, Extend the Home with Over 500 SF of Covered Outdoor Living Space, Featuring New Epoxy Flooring, a Carport Hanging Swing, Direct Lanai Access to the Paver Patio, Outdoor Fire Pit & Grill Area, and a Pea Gravel Path from the Carport to the Keyed Backyard Gate…The Grounds Have Been Curated with a Six-Figure Landscape & Lighting Package, Fully Fenced, Double-Gated Privacy, Mature Junipers, Lush Clusia Hedges, Olive Trees, Bird of Paradise, and Fragrant Jasmine…A Three-Bedroom, One-and-a-Half-Bath Residence in the Heart & Soul of Arlington Park—Just Two Blocks to Arlington Park & Aquatic Center with a 50-Meter Lap Pool, 25-Yard Instructional Pool, Indoor Pickleball, Outdoor Tennis, Basketball, Fitness Amenities, Playground, Dog Park, Picnic & Seating Areas, Public Art, Restrooms, Water Features, and a Half-Mile Walking Trail…Moments to Legacy Trail, Sarasota Memorial Hospital, Downtown Sarasota, Siesta Key, Longboat Key, Anna Maria Island, UTC Mall, and Dining & Cultural Offerings Favored by Locals…Just Fifteen Minutes to Sarasota-Bradenton International Airport…Weekly Rentals Are Allowed, Not in a Flood Zone, No Storm Damage, No HOA, and Offered Turn-Key Furnished or Curated to Buyer Preferences…Passed Down Through Only Two Owners Since the 1950s, This Home Represents Stewardship, Architectural Lineage, and Forward-Thinking Living…Timeless, Intentional, and Unmistakably Rare…Schedule Your Private Tour Today & Live a Fuller Life!
Listing is courtesy of: FULLER GROUP (941-961-3100)
Listing Agent: Bo Fuller (941-961-3100)
1761 SIESTA DR, SARASOTA, FL 34239
$1,100,00049 Days on yellowkey MLS ID: A4688614
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 2020 Built: 1949 Tax: $4,880 (2025)Community: BayviewApartment
Taxes:$4,880
Remarks: Under contract-accepting backup offers. Siesta Key Triplex – High-Yield, Weekly Rental Zoned Investment! Concrete triplex in city limits featuring one 2BR/2BA and two 1BR/1BA units with long-term tenants in place...immediate cash flow from day one. Proven income of $65K–$85K annually with low overhead expenses (taxes, insurance, landscaping only). Tenants pay all utilities with separate electric & water meters for each unit. Weekly rental zoning in city limits is a major upside for short-term income potential. Ideal for investors looking to significantly increase returns or house-hack by living in one unit and renting the others. Recent upgrades include new A/C systems, water heaters, appliances, security cameras, exterior lighting, and tropical landscaping. Solid concrete construction in Evacuation Zone D and NO flood insurance is required. Prime location just minutes to Siesta Key Beach, walking distance to dining, shopping, and essentials. Quick access on/off the key only 2 blocks to North Bridge. Value-add opportunity: Purchase adjacent property at 1760 Wisconsin Lane to scale to a 7+ unit portfolio with potential six-figure+ income. Why buy just one when you can buy both! Strong in-place income makes this a rare Siesta Key investment. Do not disturb tenants. Showings by appointment only; listing agent must accompany all showings.
2177 SUNNYSIDE PL, SARASOTA, FL 34239
$2,650,000165 Days on yellowkey MLS ID: A4674289
REDUCED by $149,000 (5.3%) on 05/05/2026
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4624 Built: 2023 Tax: $25,349 (2024)Community: Hibiscus Park 2Spa: YesSingle Family
Taxes:$25,349
Remarks: Everything you thought you needed—and knew you wanted—now offered with an unmatched level of value and flexibility. Recently repositioned with an attractive price improvement and now offered turnkey furnished, this exceptional newer construction residence presents a rare opportunity to step into luxury living—or a high-performing rental investment—without delay. Located within the City of Sarasota limits, this home allows for weekly (7-day minimum) rentals, making it uniquely suited for those seeking both personal enjoyment and income potential. The thoughtfully curated furnishings create an immediate, seamless transition for ownership or rental readiness, blending style, comfort, and functionality throughout. Designed to elevate both lifestyle and longevity, the home features a custom ProTee golf simulator, a two-person Equinox infrared sauna, and a Renu Therapy cold plunge, offering a private wellness retreat rarely found in residential properties. Spanning over 5,400 square feet of total living space, the home showcases a clean, contemporary design with expansive glass, natural textures, and effortless indoor-outdoor flow. The resort-style outdoor setting, complete with pool, spa, and dual covered entertaining areas, pairs perfectly with the home’s open interior spaces, state-of-the-art kitchen, and dedicated home theater—creating an environment equally suited for relaxation or hosting. Positioned between Southgate, Arlington Park, and Cherokee Park, and just moments from Southside Village, this residence delivers not only luxury and location, but now an exceptional opportunity to secure a fully realized lifestyle—ready to be enjoyed from day one.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Rudy Dudon (941-234-3991)
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