Location: Sarasota
Keyword(s): Booker Middle
Keyword(s) Middle School: Booker Middle
Do Not Show Listings
5462 CYNTHIA LN, SARASOTA, FL 34235
$377,000Listed 04/02/2026 3:36PM MLS ID: A4688208
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1410 Built: 1994Monthly Fee: $31 Tax: $2,019 (2025)Community: Deer Hollow Unit 6Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,019
Elementary School: Gocio Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Nestled on a quiet cul-de-sac in the sought-after Woods community, this charming 3-bedroom, 2-bathroom home offers 1,410 square feet of comfortable Florida living — priced at appraised value and ready for its next chapter. From the moment you arrive, the wide concrete driveway, mature tropical landscaping, and inviting curb appeal set the tone. Step inside to a bright, open living space with soaring vaulted ceilings and ceiling fans that keep the Florida breeze flowing year-round. Neutral carpet and a clean, move-in-ready palette make it easy to envision your personal touch throughout. The kitchen is both stylish and functional, featuring white shaker-style cabinetry, rich dark granite countertops, a double stainless steel sink, and white appliances — all bathed in natural light from a garden window overlooking the lush backyard. A convenient dining nook with light wood flooring and pendant lighting sits just off the kitchen, perfect for everyday meals or entertaining. All three bedrooms are generously sized with ceiling fans and plush carpet. The primary suite is a true retreat, boasting direct access through sliding glass doors to the screened lanai, a walk-in closet, and a private en-suite bath with a wood vanity, stone countertop, brushed nickel fixtures, and a glass-enclosed walk-in shower. Out back, the screened lanai with its own ceiling fan is the ideal spot to enjoy Sarasota's beautiful weather in comfort — overlooking a fully fenced, private backyard with a storage shed for all your extras. A spacious 2-car garage with built-in workbench rounds out this home's practical appeal. Located just minutes from Benderson Park, University Town Center, and Bobby Jones Golf Course, and with easy access to I-75 and all that Sarasota has to offer — this one checks every box. Don't miss your chance to own in The Woods at appraised value!
Listing is courtesy of: BEYOND REALTY LLC (941-467-4673)
Listing Agent: Darren Dowling (941-204-0493)
5204 MYRTLE WOOD #2, SARASOTA, FL 34235
$239,000Listed 04/03/2026 10:50AM MLS ID: A4688658
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1064 Built: 1981 Tax: $3,047 (2025)Community: SomersetCondo
Taxes:$3,047
Remarks: This move-in-ready villa offers effortless Florida is located within The Meadows, an active outdoor lifestyle community.. Steps from one of the community pools, walk to the pool from your Lanai, or sip your morning cup of coffee looking out to the pool. This condo offers both privacy and access to everything that makes The Meadows. The split-bedroom floor plan offers privacy and flexibility, with a private primary The main bedroom has a walk-in shower. The Meadows has a 1,650-acre park-like community with over 14 miles of trails, lakes, and an optional membership to golf, tennis, pickleball, and a fitness center. Just minutes from shopping and dining, downtown Sarasota, and the beaches of Siesta Key and Lido Key. Perfect for that seasonal owner or year-round resident.
Listing is courtesy of: LA ROSA REALTY LLC (941-248-2233)
Listing Agent: Rosa Arroyo (786-205-7223)
845 BENJAMIN FRANKLIN DR #302, SARASOTA, FL 34236
$444,00025 Days on yellowkey MLS ID: A4685441
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 756 Built: 1974 Tax: $5,928 (2025)Community: Presidential TheCondo
Taxes:$5,928
Elementary School: Southside Elementary
High School: Sarasota High
Remarks: BEACH LOVERS WANTED! You can experience the Lido Key lifestyle daily in this updated 1-bedroom + den 3rd floor Condo with pool and peakaboo view of the Gulf of Mexico. Ideally located directly across from Lido Beach and a short walk to St. Armand Circle, Ted Sperling Park, and Lido Beach Park. Perfect for easy beach-to-door living!! With only 40 Units, this Boutique Community is your perfect hideaway. The property abounds with palm trees and exotic plants. There is elevator access or two sets of stairs. Recent Condo updates include custom reclaimed wood kitchen & bathroom cabinetry (from the Brooklyn Shipyard), newer appliances-stone tiled bathroom- air conditioning-hot water heater-and impact sliding doors. Being offered completely furnished (*except some artwork, antiques)- just bring your suitcases! The Bayrunner Trolley stops out front and is free. Enjoy Sarasota's extensive Arts, Restaurants and nightlife without ever worrying about parking after your day in the sun. Make an appointment to see this gem now.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Wayne Fastzkie (941-315-0442)
5370 MYRTLE WOOD #56, SARASOTA, FL 34235
$224,900119 Days on yellowkey MLS ID: A4674030
REDUCED by $15,000 (6.3%) on 04/03/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1080 Built: 1981 Tax: $2,969 (2024)Community: SomersetVilla
Taxes:$2,969
Elementary School: Emma E. Booker Elementary
Tax Year: 2024
Remarks: New Improved Price!! This stunning end-unit condo offers the perfect blend of modern comfort and convenient location in The Meadows, just outside of Sarasota's desirable University Town Center area. With two bedrooms and two bathrooms spread across 1,080 square feet, this well-appointed home features freshly installed white shaker kitchen cabinets paired with elegant stone countertops that'll make your morning coffee routine feel like a luxury experience. Natural light floods the space through thoughtfully positioned windows, while vaulted ceilings create an airy, spacious atmosphere that makes entertaining a breeze. Updated modern ceiling fans and light fixtures add contemporary flair throughout, and the partially furnished setup means you can move in and start living the good life immediately. Location-wise, you've hit the jackpot. Shopping and dining options abound in the nearby University Town Center Mall corridor, with everything from casual bites to upscale restaurants just minutes away. Adventure seekers will appreciate close proximity to Nathan Benderson Park for outdoor activities, while the Mote Science Education Aquarium and PopStroke provide entertainment options. When you're ready to explore further, downtown Sarasota and pristine area beaches are just a comfortable twenty-minute drive away. This property presents an excellent opportunity for both primary residence and rental income potential, given its prime location and move-in ready condition.
Listing is courtesy of: STERLING REALTY (941-379-5810)
Listing Agent: Shaun Cumston (941-737-3539)
514 HOWARD CT, SARASOTA, FL 34236
$749,000240 Days on yellowkey MLS ID: A4660394
Bed: 4 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1606 Built: 2005 Tax: $5,700 (2024)Community: Howard CourtSingle Family
Taxes:$5,700
Elementary School: Alta Vista Elementary
Remarks: Home is locate across from Rosemary & Thyme Restaurant at 500 N. Orange Avenue- Howard Court sign is missing due to Hurricane Milton, This newer home(2005) shows very little usage and comes fully TURN KEY FURNISHED. It has a side entrance door which leads to the first/ second floors and the garage. Bamboo floors and crown molding enhances this home along with 2 covered screened lanais. You will enjoy a one oversized garage along with two heating/ac units one for each level. The upstairs unit is perfect for family, companion or care giver. Each floor has a bathroom and living room. Howard Court is 2 blocks to Fruitville Road. This is a must see home for annual, seasonal or use for family members to visit. There are only 4 homes in Howard Court Subdivision close to CBD area off Orange Avenue. Howard Court street is maintained by owner. SEEING IS BELIEVING !!
Listing is courtesy of: RON STAHL REALTY (941-374-1671)
Listing Agent: Ronald Stahl (941-374-1671)
516 HOWARD CT, SARASOTA, FL 34236
$749,000241 Days on yellowkey MLS ID: A4660708
Bed: 4 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1622 Built: 2005 Tax: $5,707 (2024)Community: Howard CourtSingle Family
Taxes:$5,707
Remarks: Home is located across from Rosemary & Thyme Restaurant at 500 N. Orange Av --Howard Court sign is missing due to Hurricane Milton. Well cared for newer(2005) 2 story home with side door entrance into the main floor and/or 2nd floor. TURN KEY FURNISHED with crown molding ,bamboo and ceramic tile flooring, 2 screened covered porches one on each floor, large one car garage, two unit AC units one for each floor. Many more features to enjoy--- upstairs has uses like mother in law suite or for a companion. Each floor has a bathroom and living room. Howard Court is 5 blocks to Main Street...... 2 blocks to Fruitville Road. This is a must see close in home in excellent condition. Only 4 homes are located in this quiet area off Orange Avenue Howard Court street is owners responsibility SEEING IS BELIEVING !!!!!!!!!
1750 BENJAMIN FRANKLIN DR #10G, SARASOTA, FL 34236
$1,175,00060 Days on yellowkey MLS ID: A4680259
REDUCED by $25,000 (2.1%) on 04/03/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1548 Built: 1970 Tax: $9,085 (2025)Community: Key Tower SouthCondo
Taxes:$9,085
Remarks: ****There is nothing left to do. Nothing to imagine. Completed in 2022, everything has been upgraded and transformed into the most modern luxury. This high-floor corner residence on Lido Beach in the Key South Tower building has been completely transformed—from ceilings to floors—into a home where every high-end creature comfort is already in place and water views unfold from every window. The building is so modern, so perfectly updated and completed that it even has its own hurricane/surge protection system surrounding the building-- unique and impressive. You must see this condo's extraordinary views in day and at night!!! ****Panoramic vistas stretch across the Gulf of Mexico, Sarasota Bay, the Ringling Bridge, and downtown Sarasota, creating a constantly shifting backdrop of light, water, and skyline. Set within a Lido Beach building that has already been elevated to the highest modern building standards, this residence offers peace of mind. The HOA’s abundant reserves reinforce the sense of security -- owners love living here. Inside, porcelain tile flows throughout, complemented by all-new ceilings and modern lighting that set a sophisticated, contemporary tone. ****The kitchen is both elegant and functional, featuring abundant new wood cabinetry, quartz countertops, and new appliances—designed for everything from casual mornings to elevated entertaining. The primary suite is a private sanctuary, framed by water views and finished with the finest luxury tile. It offers a walk-in closet, an ensuite bath with a walk-in shower, and thoughtful storage. The guest suite is equally impressive, with new tile, a walk-in closet, and beautiful views of the Intracoastal Waterway and downtown Sarasota. Spacious enough for a king bed, it also features its own walk-in shower, making it ideal for guests who appreciate comfort and privacy. ****Beyond the residence, Key Tower South has been fully reimagined, with the lobby and common areas completely renovated in 2025. Residents enjoy 220 feet of private Gulf frontage, a heated beachfront pool, expansive sundeck, direct beach access, saunas, a fitness room, library, bike storage, and on-site management—resort-level amenities without the crowds. ****This is not simply a condo. It is a fully realized beachfront lifestyle—elegant, effortless, and complete. Call now for a private showing. Prefer to experience it from afar? Drone footage and immersive fly-throughs are available.
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: Meredith Van Vaals (612-716-4784)
5174 MARSH FIELD LN #86, SARASOTA, FL 34235
$290,000Listed 04/03/2026 12:13AM MLS ID: TB8484850
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1444 Built: 1981 Tax: $3,593 (2025)Community: Heronmere IiCondo
Taxes:$3,593
Remarks: Welcome to this beautifully updated corner-unit condo in the highly desirable Heronmere II community within The Meadows in Sarasota. Offering 2 bedrooms, 2 bathrooms, and approximately 1,444 square feet of living space, this light-filled residence blends timeless architecture with modern comfort. Designed with an open and airy layout, the home is filled with natural light from multiple exposures, enhancing the spacious living and dining areas. The updated kitchen features ample cabinetry, generous workspace, and large windows—perfect for both everyday living and entertaining. The primary suite offers a private retreat with a walk-in closet and renovated en-suite bath, while the second bedroom provides flexibility for guests or a home office. An enclosed lanai invites you to relax and enjoy peaceful golf course and lush landscape views year-round. Additional highlights include an in-unit laundry room, covered parking, and access to a community pool. Residents of The Meadows enjoy scenic walking trails, mature landscaping, and optional memberships for golf, tennis, and social amenities. Ideally located just minutes from shopping and dining at University Town Center, with convenient access to I-75 and only a short drive to downtown Sarasota’s vibrant arts scene and Gulf Coast beaches, this move-in-ready condo offers the perfect combination of lifestyle, location, and value.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Adam Arucas (813-380-1840)
2332 SEWARD DR, SARASOTA, FL 34234
$345,00031 Days on yellowkey MLS ID: D6146339
REDUCED by $5,000 (1.4%) on 04/03/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 928 Built: 1985 Tax: $2,904 (2025)Community: Spring OaksSingle Family
Taxes:$2,904
Remarks: Short Sale. Welcome to this unique 2-bedroom, 2-bath pool home in beautiful North Sarasota, Florida! This charming property backs up to a peaceful preserve, offering added privacy with no rear neighbors — no one can build behind you. The home features fresh exterior paint, giving it great curb appeal, along with a fully fenced yard perfect for pets, entertaining, or simply enjoying your own private outdoor space. Conveniently located near shopping, dining, and entertainment, you’ll love the easy access to everything Sarasota has to offer while still enjoying a quiet neighborhood setting. This is a wonderful opportunity for first-time homebuyers, seasonal residents, or anyone looking for a cozy Florida retreat with a pool and privacy. Don’t miss your chance to make this North Sarasota gem your own!
Listing is courtesy of: CENTURY 21 SUNBELT REALTY (941-625-6120)
Listing Agent: Jayson Burtch (941-626-5432)
435 S GULFSTREAM AVE #1004, SARASOTA, FL 34236
$950,000151 Days on yellowkey MLS ID: A4670726
REDUCED by $45,000 (4.5%) on 04/03/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1829 Built: 1972 Tax: $10,813 (2025)Community: Regency HouseCondo
Taxes:$10,813
Remarks: One or more photo(s) has been virtually staged. Welcome to Regency House, nestled in the heart of Sarasota on a serene, tree-lined street—ideally located between Gulfstream and Palm Avenue. Enjoy sweeping views of Sarasota Bay, breathtaking sunsets, and effortless walkability to the city’s premier dining, shopping, cultural attractions, and the bayfront. This beautifully updated 1,829 sq. ft. residence is designed with both style and function in mind, featuring a spacious split floor plan that maximizes privacy. The living room opens to spectacular north- and west-facing views, where sparkling city lights, Marina Jack’s Park, and Sarasota Bay create a stunning backdrop. Thoughtfully integrated shelving adds versatility and easily adapts to a dedicated home office set up. Modern upgrades include new flooring, a fresh neutral palette, and a sleek kitchen with stainless LG appliances and a Bosch induction cooktop. With abundant storage and generous counter space, the kitchen is ready for everything from casual meals to lively entertaining. Each bedroom is a private retreat, offering gorgeous sunset views, updated baths, and abundant closet space—including brand-new $50,000 custom organizers. A versatile bonus/storage room provides additional flexibility for work, hobbies, or extra belongings. Resort-style amenities enhance everyday living: a heated pool, fitness center, stylish club room with catering kitchen, and the peace of mind of 24/7 concierge service. A full-size, in-residence washer and dryer make this home as practical as it is luxurious.Don’t miss this rare opportunity to experience vibrant downtown living with every convenience right at your doorstep.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Dianne Anderson (941-350-3513)
4018 PRADO DR, SARASOTA, FL 34235
$459,000Listed 04/03/2026 9:11AM MLS ID: A4688500
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1842 Built: 1969 Tax: $2,873 (2025)Community: De Soto LakesSingle Family
Taxes:$2,873
Remarks: Welcome to this spacious 4-bedroom, 2-bath home featuring an open floor plan that seamlessly connects the kitchen, dining, and living areas—perfect for entertaining or relaxing with family. The large kitchen offers plenty of workspace and storage, while the bonus/family room adds flexibility for a playroom, home office, or media space. The primary suite includes a walk-in shower and an upgraded closet system for extra organization. Throughout the home, you’ll find ceiling fans, ceramic tile and vinyl floors (no carpet), and an inside laundry room. Major updates bring peace of mind: HVAC (2024), water heater (2019), roof (2015), and a new garbage disposal. Step outside to a fully fenced, oversized backyard—ideal for pets, outdoor living, or adding a pool. A large storage shed provides additional space for tools and toys. With no HOA restrictions, you’ll have the freedom to make this property truly your own. Conveniently located near shops, restaurants, the airport, and Sarasota’s world-famous beaches, this move-in-ready home offers comfort, functionality, and a prime location for your Florida lifestyle.
Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE (941-556-9100)
Listing Agent: Lynda Ellinger, Pa (941-228-2430)
800 N TAMIAMI TRL #1603, SARASOTA, FL 34236
$1,895,000163 Days on yellowkey MLS ID: A4669042
Bed: 2 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2471 Built: 2007 Tax: $23,269 (2025)Community: AlinariCondo
Taxes:$23,269
Elementary School: Bay Haven Sch of Basics Plus Elementary
Remarks: PRICE IMPROVEMENT! Perched high above Sarasota Bay with breathtaking bay views, this two-story luxury penthouse at Alinari is your private sanctuary in the sky where New York loft style meets the beauty and energy of Florida's most cultured coastal city. Enjoy this Sarasota Downtown pied-a-terre where the views of the azure, blue Bay waters greet you from every window, even when you are luxuriating in your private spa tub! This architectural masterpiece was completely redesigned and reimagined in 2020-2023 by leading architect Yehuda Inbar and custom builder Yoder Homes and fuses architectural drama with coastal ease. A soaring 20-foot atrium fills the open plan with natural light, framing dazzling and protected water views of the Bay, Bayfront Park and the Van Wezel Performing Arts Hall just across the street. Polished concrete, Caesarstone quartz, and fine Ceramiche D'Arte porcelain floors set a modern tone, softened by custom draperies and curated furnishings that invite lingering afternoons and golden sunsets. The 2500 square-foot, 2/3 bedroom, 3.5 bath floor plan features a chef's kitchen, statement staircase, and loft-style layout which recalls a Manhattan gallery, while the upper-level primary suite offers a serene retreat with a spa-like bath. The condo can easily be converted to a full 3 bedrooms, with each bedroom featuring an en-suite bath. Smart-home features, cutting edge Integrity Sound audio system, Dimplex fireplace, electric shades, and turnkey interiors with premium furnishings from Clive Daniel, Natuzzi, Soft Square and Light Up Your Life complete a space made for effortless sophistication. Open the sliders to your private balcony and savor gentle bay breezes while taking in the picturesque surroundings. Alinari's resort amenities elevate everyday living with a resort-length pool, heated spa, yoga and fitness studios, saunas, wine cellar, theater, social and billiards lounges, guest suites, 24/7concierge/security, and 2 spaces in the secure garage parking. Available separately, a private poolside cabana one of only ten adds an intimate escape with kitchenette and direct pool access, perfect for entertaining or quiet retreat. Set 16 feet above sea level in a protected X-flood zone and steps from the signature 53-acre Bayfront Park and Sarasota's vibrant dining arts, and cultural offerings, this penthouse embodies cultured coastal living at its most graceful, artful, uplifting, and one of a kind.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lenore Treiman (941-356-9642)
1350 MAIN ST #PH1600, SARASOTA, FL 34236
$1,995,000178 Days on yellowkey MLS ID: A4666660
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2165 Built: 2007 Tax: $14,766 (2025)Community: 1350 Main ResidentialCondo
Taxes:$14,766
Remarks: One or more photo(s) has been virtually staged. Rarely available penthouse on the 16th floor of sought-after 1350 Main in the heart of Downtown Sarasota! This beautiful 3-bedroom, 3-bath corner residence showcases spectacular Bay and city vistas from every room, upscale finishes and craftsmanship, and a wonderful open floor plan. Upon entry to the great room, you will enjoy the open light-filled room with 10' ceiling (only available on the top 3 floors), exquisite built-in, great space to showcase your personal art collection, and large terrace to relax and enjoy the bay breezes. The updated open-concept kitchen features stainless appliances including a high-end Thermador Professional-style gas range with 6-burner cooktop, 2 electric ovens, large center island, solid wood cabinetry, beautiful stone counters, and walk-in pantry. The split plan design boasts 3 spacious en-suite bedrooms including the primary bedroom with private terrace, custom walk-in closet and updated luxurious en-suite bath. Beautiful, engineered hardwood and ceramic tile floors throughout. 1350 Main is known for its great location, 24-hour concierge and on-site manager, secure entry, pet friendly building, and wonderful amenities including heated resort style pool and spa, recreation deck with gas grill, fire pit, herb garden, fitness center, steam rooms, guest suite, catering kitchen, social and conference/business rooms, electric car charging stations, and water softener/filtration in the entire building. The premier Downtown Sarasota address is perfect for proximity to all the cultural venues, art galleries, boutiques, Saturday farmers market, festivals, great restaurants, and proximity to the #1 Siesta Key Beach, Lido, and Longboat Keys.
1685 6TH ST, SARASOTA, FL 34236
$1,650,000178 Days on yellowkey MLS ID: A4667628
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2938 Built: 1997 Tax: $6,942 (2025)Community: Halls Sub James SSingle Family
Taxes:$6,942
Remarks: PRICE IMPROVEMENT! Perfectly situated in Sarasota’s vibrant Downtown just minutes from restaurants and boutiques within the coveted Gillespie Park neighborhood, this beautifully renovated 2,938 sf, 4-bedroom, two-story Key West–inspired pool home blends timeless architectural charm with modern sophistication. A magnificent oak tree graces the front yard, framing the home’s welcoming façade, while a historic brick driveway—crafted from original Sarasota street bricks—sets the stage for the artistry and attention to detail found throughout. Remodeled and expanded, the interior showcases solid wood floors, designer lighting, and refined finishes which create a warm yet elegant ambiance. The gourmet kitchen impresses with custom cabinetry with soft-close drawers, quartz countertops, and top-tier appliances including a professional Forno gas range. Open-concept living and dining spaces are enhanced by an electric fireplace and abundant natural light streaming through windows and doors, many of which are impact-rated. Upstairs, rich hardwood flooring continues through the private quarters, including the serene primary suite featuring a custom-built walk-in closet and a spa-inspired bath adorned with porcelain tile, and designer fixtures. A downstairs bonus area—currently used as a Pilates studio with private entry—is zoned for business or rental use and could easily serve as a large luxurious primary suite, family room, media room, or fitness space. A beautifully designed 600 sf apartment provides fully independent or multi-generational living with its own contemporary kitchen, induction cooktop, full-size washer and dryer, and private balcony. Perfect for hosting guests, mother-in-law suite, extended family, or generating income, this versatile space has a separate entrance, parking spot and its own address, and qualifies for one-week rentals. Additional highlights include a temperature-controlled wine room, an oversized laundry room, three zoned AC, and a security system. Outside, a lush courtyard with screened lanai and heated pool creates a tranquil retreat for relaxing or entertaining amid tropical landscaping. Set on a spacious, fenced corner lot, the property offers abundant privacy along with an expanded 2½-car garage featuring an impact-rated door and generous storage. Residents of Gillespie Park enjoy one of downtown Sarasota’s most walkable locations—just moments from Main Street and the new Bayfront Park where you can catch sunset, take in water views while enjoying a concert, yoga or lounging with your feet in the sand. Enjoy nearby fine dining, boutique shopping, arts and cultural venues, and easy access to SRQ International airport. The neighborhood’s namesake park offers tennis and pickleball courts, dog areas, and a lively community spirit that captures the essence of urban Sarasota living. Blending the character of Sarasota’s historic past with the ease of modern luxury, this exceptional residence delivers rare flexibility, craftsmanship, and an enviable location in the heart of it all.
383 BOBBY JONES RD #383, SARASOTA, FL 34232
$199,000323 Days on yellowkey MLS ID: A4652341
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1334 Built: 2003 Tax: $2,619 (2025)Community: BrooksideCondo
Taxes:$2,619
Remarks: $20,000 PRICE REDUCTION ON THIS NEWLY RENOVATED ground floor 2-bedroom, 2-bathroom condominium with beautiful golf course views, well-located for the utmost of privacy at the end of the serene and well-maintained Hideaway community, just minutes to Downtown Sarasota. Welcome to this smartly updated move-in-ready residence which offers the perfect blend of modern comfort, efficient design, and a picturesque setting with direct views of the lush newly redesigned Bobby Jones Golf Course from your screened-in patio—ideal for morning coffee or evening relaxation. Step inside to discover a freshly renovated interior including brand-new luxury vinyl wide plank flooring, updated kitchen and baths with new cabinetry and stone counters, designer ceiling fans with lights, and new impact windows. The floor plan is both functional and inviting, with a spacious living area, separate dining room, and an open feel that makes entertaining a breeze. The primary suite is generously sized and offers a tranquil golf course view, a large closet, and an updated ensuite bath with stone-topped vanity. The guest bedroom is perfect for visitors or a home office, with access to an updated and well-appointed second full bath. Additional highlights include a brand-new full-size washer and dryer in-unit, new water heater, abundant closet space and plenty of natural light throughout. This unit also comes with two prime parking spaces located just steps from the front door. The Hideaway offers a great lifestyle with lush landscaping, mature oak trees, two community pools, and scenic walking trails. The low-maintenance condo fee includes exterior maintenance as well as water, sewer, trash, pest control, and pool service—providing true ease of ownership. With no CDD fees, no age restrictions, and flexible leasing policies, this community is ideal for full-time living, a seasonal getaway, or a smart investment opportunity. Perfectly situated close to Downtown Sarasota, the Legacy Trail, SRQ Airport, I-75 and some of Florida’s most celebrated Gulf Coast beaches, this gem combines location and low-cost living in one of Sarasota’s most convenient communities.
5310 N TUTTLE AVE, SARASOTA, FL 34234
$850,0008 Days on yellowkey MLS ID: A4685035
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2408 Built: 1956 Tax: $7,598 (2025)Community: Desoto AcresSingle Family
Taxes:$7,598
Remarks: Invest in one of central Sarasota’s most versatile acreage opportunities with this gated 2.23-acre RE1-zoned estate in the historic Desoto Acres community, offering rare land-use flexibility with no active HOA and no enforced deed restrictions. Positioned for future growth, the property is fully secured with perimeter fencing and an electronic security gate at the 53rd Street entrance, with dual asphalt driveways already installed to support expanded use. A cleared and prepped secondary build site provides immediate potential for a detached guest house, ADU, or professional-grade workshop. Approximately $106,000 in recent capital improvements—including a 2023 roof, 2019 HVAC, new water heater, heavy-duty double septic system with lift station, and a deep-drilled 251-ft well recently rejetted with a brand-new submersible pump—significantly reduce future infrastructure costs and strengthen development readiness. While the existing residence is dated, it is fully functional and refreshed with a brand-new mini-split system in the owner’s suite, providing immediate climate-controlled comfort for a primary resident or a phased renovation project. A four-car garage configuration includes an oversized attached two-car garage and a detached air-conditioned workshop, plus 50-amp RV hookups to accommodate specialty storage needs. Located just minutes from UTC and downtown Sarasota, this property represents a strategic land-bank or custom compound opportunity with substantial upside potential. This is a rare find for the buyer who values independence, infrastructure, and a blank canvas for their Florida lifestyle. Schedule your private tour and evaluate the possibilities today.
Listing Agent: Tory Uccello, Jr (941-504-8052)
1064 N TAMIAMI TRL #1308, SARASOTA, FL 34236
$375,000167 Days on yellowkey MLS ID: A4668948
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 985 Built: 2007 Tax: $4,426 (2024)Community: Broadway PromenadeCondo
Taxes:$4,426
Elementary School: Gulf Gate Elementary
High School: Riverview High
Remarks: Welcome to Broadway Promenade - Sarasota Living at Its Best! Located in the heart of Sarasota’s renowned Cultural Arts District, this beautifully maintained and charmingly furnished 2-bedroom, 2-bath condo on the 3rd floor offers the perfect blend of style, comfort, and convenience. Being sold turnkey, it is ready for you to move right in. Whether you are looking for a full-time residence or a seasonal retreat, this condo makes it easy to enjoy everything Sarasota has to offer. This unit boasts a spacious open layout filled with abundant natural light, an separate owner storage room for added convenience and a trash chute right on the floor for easy disposal. Resort-style amenities include a sparkling pool and spa, fitness center with locker rooms and saunas, business center with computer, printer, and internet access, billiards, card room, library, and social club room. There’s also 24/7 concierge service, secured FOB access, and on-site management and maintenance. For visiting guests, there are four beautifully renovated, fully furnished guest suites available to rent. Unmatched location with an on-site Publix grocery store and nearby shopping and dining for ultimate convenience. Just minutes to theaters, art galleries, cultural events, parks, marina, and world-famous Gulf Coast beaches. Broadway Promenade offers an elevated lifestyle where every detail is designed for ease and enjoyment. If you have been waiting for a Sarasota condo that checks all the boxes - style, security, amenities, and location - this is it!
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Tina Renta (941-600-7361)
435 S GULFSTREAM AVE #403, SARASOTA, FL 34236
$689,000176 Days on yellowkey MLS ID: A4667640
REDUCED by $5,500 (0.8%) on 04/03/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1424 Built: 1972Monthly Fee: $1,393 Tax: $8,165 (2024)Community: Regency HouseCondo
Taxes:$8,165
Remarks: One or more photo(s) has been virtually staged. SELLER SAYS: “MAKE THIS CONDO YOURS TODAY!” All assessments paid by seller**** (Translation: Don’t wait… this view won’t.) Welcome to your front-row seat to Sarasota Bay at the highly sought-after Regency House on Gulfstream Avenue. This beautifully updated 2-bedroom, 2-bath residence sits on the 4th floor and offers 1,424 sq. ft. of bright, open living space—plus a wall of floor-to-ceiling windows that deliver sparkling bay views from morning coffee to sunset cocktails. The open-concept living and dining areas are flooded with natural light (yes, it’s as good as it sounds), while the designer kitchen features stone countertops, custom cabinetry, and stainless-steel appliances—perfect for hosting, entertaining, or simply enjoying the view while pretending you’re on vacation. The primary suite is a peaceful retreat with panoramic water views, a generous closet, and a beautifully updated ensuite bath. The second bedroom is equally spacious and flexible—ideal for guests, a home office, or a stylish retreat of your own. Residents of Regency House enjoy resort-style amenities including a 24-hour concierge, heated pool, updated clubroom, and secure covered parking—all designed for effortless downtown living. Located just steps from Marina Jack, Bayfront Park, Main Street dining, shopping, galleries, and Sarasota’s vibrant arts and cultural scene, this is downtown waterfront living done right. Easy to schedule showings. Come see why this is one of the BEST values on the Bayfront—and why you’ll want to act fast.
Listing is courtesy of: MEDWAY REALTY (941-375-2456)
Listing Agent: Kim Donahue (941-724-2587)
2107 CHIPPAWA PL, SARASOTA, FL 34234
$485,000Listed 04/02/2026 8:29PM MLS ID: A4688520
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1348 Built: 1950 Tax: $5,429 (2025)Community: Sylvan ShoresSingle Family
Taxes:$5,429
Remarks: Located West of the Trail in the Indian Beach / Sapphire Shores neighborhood of Sarasota, this single-family property offers flexible living with an additional efficiency. The main residence includes 2 bedrooms and 1 bathroom, featuring a newly updated kitchen, along with a separate laundry room for added convenience. Natural light and a functional layout create comfortable everyday living. The spacious backyard offers room for outdoor enjoyment and entertaining. A standout feature of the property is the separate 1 bedroom, 1 bathroom grandfathered-in efficiency with its own private entry and private yard, providing flexibility for rental use. Total living configuration includes 3 bedrooms and 2 bathrooms across both living spaces. No deed restriction. The home is located in an X flood zone where flood insurance is NOT required. The property is located in proximity to nearby points of interest including The Ringling Museum, Sarasota Jungle Gardens, Ringling College, New College, USF Sarasota-Manatee, Asolo Repertory Theatre, and The Bay. Convenient proximity to downtown Sarasota and the Rosemary District offer access to dining, shopping, and cultural amenities, while Lido Key provides nearby beach access. Optional Indian Beach Sapphire Shores neighborhood association offers a neighborhood newsletter, picnic, and additional social activities. Property is being sold as-is.
Listing is courtesy of: BROOKFIELD REAL ESTATE LLC (941-917-0494)
Listing Agent: Eric Collin (941-350-7775)
761 JOHN RINGLING BLVD #31, SARASOTA, FL 34236
$675,0001 Day on yellowkey MLS ID: A4688346
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 816 Built: 1963 Tax: $6,923 (2025)Community: Sarasota Harbor WestCondo
Taxes:$6,923
Remarks: Exquisite FURNISHED interior designer owned condo epitomizing refined coastal living in Sarasota and completely renovated down to the studs in 2019-2020. Interiors are enveloped in a meticulous pallet of ocean-inspired hues that blends timeless style with modern functionality and coastal glam charm. Island living is yours with the most incredible location less than one block to St. Armand’s Circle and a short jaunt from the beach, parks, wildlife centers, 3 yacht & sailing clubs, downtown, The Ritz Carlton, The St. Regis, and a plethora of boutique shops and restaurants. Enjoy breathtaking sunset & turquoise water views from every room over Sarasota Bay and beyond to the Keys. Watching dolphins play and manatees swim along the seawall below your balcony will be a daily occurrence. A more well positioned unit does not exist in Sarasota Harbor (top floor, end unit, Western facing, closest to the water, and closest building to the circle). Professionally envisioned by this talented designer/owner and masterfully executed by a long-standing, local, luxury builder with no expense spared. Entirely new infrastructure, including complete drywall replacement, floors, and raised ceilings, new HVAC and ductwork, in-wall sound insulation, double insulated attic, new electrical panel including wiring in walls, all new plumbing throughout, new 40-gallon water heater, and more. This unit is ultimate storm ready including PGT impact windows and doors and withstood the unprecedented 2024 storm season with incredible resilience and zero damage. The thoughtfully crafted kitchen features only the best of Miele, Sub-Zero and Viking appliances, Waterstone fixtures that shine beneath bespoke lighting, an artist commissioned mosaic, and a hand-forged range hood. A large under-lit quartzite island can seat 6, bench built solid wood Albrecht cabinetry with pullouts, under cabinet outlets, paneled appliances, Cambria 6cm custom profile back countertops, and grout-less sea glass backsplash ensure any chef a seamless experience. The magic is in the details and this unit is a work of art unto itself but within you will find a curated collection of salvaged nautical antique accents from across the world, artwork paying homage to Sarasota’s history, an authentic nautical porthole from a German ship, and master carpentry features such as tongue and groove ceilings, solid wood doors, shiplap accents, 7” stacked crown moldings, 5” baseboards, plantation shutters, and built ins with color changing Dimplex fireplace. The excellence does not stop here...every room includes recessed gimbal lighting with Maestro dimmers, the spa-inspired bathrooms glimmer with custom tile work, hammered nickel sinks, a seamless glass shower, Rohl polished nickel fixtures, hotel double towel racks, heat lamps, Helios LED smart mirrors, and other luxe finishes. Besides the unbeatable location, residents of Sarasota Harbor West enjoy an array of inclusive amenities that include a large heated waterfront pool, clubhouse, shuffleboard, fishing pier, and grill areas. End unit balconies can be screened-in with HOA design approval. Non-deeded boat slips are available for a very small fee on a first-come basis.
Listing is courtesy of: WINKLE AND COMPANY LLC (941-500-9731)
Listing Agent: Holly Winkle (941-500-9731)
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