Location: Sarasota
Keyword(s): Booker Middle
Keyword(s) Middle School: Booker Middle
Do Not Show Listings
435 S GULFSTREAM AVE #1004, SARASOTA, FL 34236
$950,000178 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 HouseSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,813
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Booker Middle
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)
217 S SHADE AVE, SARASOTA, FL 34237
$1,899,000420 Days on yellowkey MLS ID: A4628117
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2561 Built: 2025 Tax: $4,777 (2023)Community: Terrace GardensSingle Family
Taxes:$4,777
Elementary School: Alta Vista Elementary
Tax Year: 2023
Remarks: Introducing THE RETREAT, a stunning two-story residence. FOUR (4) bedroom, THREE (3) bath. Paver driveway, 3 CAR GARAGE, LVP flooring. Home has been professionally staged. Pool is complete; size 12 x 26 , leaving plenty of green space for pets in the backyard! This exceptional new build boasts superior block construction, a durable metal roof, impact-resistant windows, doors, and sliders. Inside is a thoughtfully designed open floor plan, featuring soaring 10-foot ceilings and elegant 8-foot solid core doors that enhance the home’s impressiveness. The gourmet kitchen is complete with a 6-foot island, luxurious quartz countertops, custom shaker cabinetry, and a top-of-the-line appliance package, perfect for both daily meals and entertaining. The primary bedroom, located on the main level, is a serene retreat with stunning tray ceilings, large his/her walk-in closets, double vanity, and a spacious walk-in shower. Bedroom #2, also on the first floor, is versatile and can serve as an additional bedroom or a home office. Upstairs, you'll find two more generously sized bedrooms that share a beautifully appointed full bathroom. The home’s detailed interior is complemented by luxury vinyl plank flooring throughout both levels, providing durability and style. Outdoors, a gas-heated saltwater pool and paver deck creates the ideal setting for relaxation and entertainment. Conveniently located with easy access to downtown Sarasota, the Legacy Trail, Payne Park, Sarasota Memorial Hospital, and the world-renowned beaches of Longboat and Siesta Keys, this home offers the perfect blend of luxury, comfort, and convenience for modern family living. Experience elevated living at its finest in "your RETREAT"!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Ingrid Caruso (941-539-6233)
2042 COUNTRY MEADOWS PL, SARASOTA, FL 34235
$515,000150 Days on yellowkey MLS ID: A4673225
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2052 Built: 1989Monthly Fee: $46 Tax: $2,868 (2024)Community: Country MeadowsSpa: NoSingle Family
Taxes:$2,868
Elementary School: Gocio Elementary
High School: Booker High
Tax Year: 2024
Remarks: LOCATION AND CONDITION ARE A+++ From the moment you arrive, you’ll feel right at home in this impeccably maintained residence. Meticulous care and attention to detail are evident throughout. The welcoming foyer opens seamlessly to the dining and living areas, offering views of the expansive lanai and oversized backyard. The beautifully remodeled kitchen is truly the heart of the home, designed to inspire and impress. Featuring porcelain tile floors, bright granite countertops, new cabinetry, and new appliances, it opens effortlessly to the family room with a cozy fireplace—perfect for both entertaining and everyday living. A smart thermostat and Ring doorbell add modern convenience and peace of mind. Whether seated at the breakfast bar or in the sunny nook beneath cathedral ceilings and skylights, you’ll appreciate the light-filled, open atmosphere. A generously sized pantry will delight any home chef. The split-bedroom floor plan provides privacy for all. Two guest bedrooms offer walk-in closets and share a roomy bath with direct lanai access. The primary suite is a true retreat, featuring a spacious walk-in closet and a stunning, newly renovated bath with updated tile flooring, new cabinetry, linen storage, and a solid-surface dual-sink vanity. Impact-resistant windows and doors are installed throughout, including private lanai access from the primary suite. Additional highlights include an oversized laundry room, ample floored attic storage, and an extended lanai designed for outdoor enjoyment—complete with granite counter space, sink, gas grill, and vented stainless-steel hood. The oversized lot provides abundant outdoor space and room for a future pool, if desired. Ideally located with convenient access to Downtown Sarasota, UTC Mall, Benderson Park, golf courses, dog parks, and recreation for all ages, this home places you just 15–20 minutes from the airport, Ringling Museum, marinas, colleges, and Lakewood Ranch Main Street. Move-in ready and thoughtfully updated, this exceptional property offers the lifestyle you’ve been waiting for. Schedule your private showing today and experience it for yourself.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Susan Keal (941-320-1689)
3150 RINGWOOD MDW #54, SARASOTA, FL 34235
$254,000163 Days on yellowkey MLS ID: A4672491
1 Days Off yellowkey (back on 4/28/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1351 Built: 1981 Tax: $3,760 (2024)Community: Villas Of PapillionVilla
Taxes:$3,760
Remarks: Villa unit in beautiful and convenient section within The Meadows. Very close to the Meadows shopping village with the new sweet treat ice cream shoppe, a new Indian cuisine restaurant and the famous Mona Lisa Italian restaurant. You can literally walk over for an evening out. You are just a mile away from UTC with the newest in shopping, dining and entertainment venues, including the newly opened Mote Marine Aquarium. Needs some updating but otherwise very nice 2 bedroom/2 bath in Villas of Papillon featuring the most unique community pool setting in the area. Accessed by little bridge the pool is located on a little island in the lake. Possessions will be removed prior to closing or can be left.
Listing is courtesy of: REALTY SERVICES INC (941-954-4443)
Listing Agent: Kenneth Cowles (941-954-4443)
2636 HIDDEN LAKE DR N #H, SARASOTA, FL 34237
$142,000100 Days on yellowkey MLS ID: A4679045
Bed: 0 Bath: 1.0 Liv Area Sq Ft: 523 Built: 1974 Tax: $1,229 (2025)Community: Hidden Lake VillageCondo
Taxes:$1,229
Elementary School: Tuttle Elementary
Remarks: New price and strong value in Hidden Lake Village! This clean 1-bedroom condo offers low-maintenance living in a central Sarasota location just minutes to downtown, beaches, and shopping. The open layout, screened lanai, and peaceful courtyard setting make this an easy property to enjoy or add to your rental portfolio. Investors will appreciate the steady rental demand in this community and the low monthly carrying costs. Hidden Lake Village offers two pools, tennis courts, fitness center, clubhouse, and on-site laundry. At $142,000, this is one of the best opportunities in the community for an affordable Sarasota property with solid long-term upside.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Greg Dudley (240-461-7460)
5201 STEVENS DR, SARASOTA, FL 34234
$615,00083 Days on yellowkey MLS ID: A4681358
Bed: 4 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2016 Built: 1958 Tax: $2,494 (2025)Community: Indian Beach EstatesSpa: NoSingle Family
Taxes:$2,494
Elementary School: Emma E. Booker Elementary
Remarks: ENJOY THE BEST OF FLORIDA LIVING in this beautifully maintained mid-century modern home. Featuring 4 bedrooms, 2 1/2 bathrooms, an extended 1 car garage and over 2000 square feet of thoughtfully designed living space. This open floor plan offers a desirable split floor plan with two en-suite bedrooms, an updated kitchen, and large family room perfect for everyday living or entertaining. For additional peace of mind there is a NEW ROOF and IMPACT WINDOWS. Step outside on your lanai where you can create your outdoor oasis or enjoy the views of the oversized backyard. Located in Sapphire Shores, this home is minutes to University Town Center, SRQ airport, Ringling Museum, Downtown Sarasota, St. Armand’s Circle, Lido Beach and offers two bay front parks providing access for water activities and views. A perfect blend of comfort, space and location – this home truly delivers a lifestyle like no other.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Angela Adams (941-809-9760)
2100 BENJAMIN FRANKLIN DR #203, SARASOTA, FL 34236
$475,000170 Days on yellowkey MLS ID: A4671669
REDUCED by $20,000 (4.0%) on 04/01/2026
Bed: 1 Bath: 1.5 Liv Area Sq Ft: 778 Built: 1968 Tax: $4,748 (2024)Community: Lido Harbour SouthCondo
Taxes:$4,748
Remarks: Enjoy beachside living at Lido Harbour South on Lido Key. This east-facing condo features one bedroom, one and a half baths, and a bright, inviting layout. The kitchen offers granite countertops and stainless steel appliances, while the enclosed Florida room, with hurricane-impact windows, a ceiling fan, and a closet, provides the perfect spot to relax and enjoy the morning light. For added convenience, a washer is located in the primary bedroom closet, with a communal laundry room on the same floor. Residents have private beach access, a community pool, and a patio area with tables, lounge chairs, and an outdoor shower - everything needed for the perfect day in the sun. In the evenings, take in breathtaking sunsets from the private beach. Ideally located near Ted Sperling Park at South Lido Key Beach, where you can explore scenic nature trails or kayak through peaceful mangrove tunnels, and only minutes from St. Armands Circle's renowned dining and boutiques and the vibrant arts and culture of Downtown Sarasota, this condo captures the essence of relaxed island living.
Listing Agent: Maria Beck, Pa (646-531-4118)
4683 WINSTON LN N #30, SARASOTA, FL 34235
$275,000184 Days on yellowkey MLS ID: A4670091
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1224 Built: 1997Monthly Fee: $669 Tax: $3,297 (2024)Community: Beekman LakesTownhouse
Taxes:$3,297
Remarks: Live the good life at Beekman Lakes! Beautifully maintained single-story 2/2 Florida contemporary lakefront villa offering 1,224 sq. ft. under air and 1,848 sq. ft. under roof! This light, bright and airy 2-bedroom, 2-bath attached villa features an open split-bedroom floor plan with vaulted ceilings, transom windows, and serene lake views. The spacious primary suite overlooks one of the community's many lakes with an illuminated fountain, setting just the right mood to relax at the end of the day! The spectacular floor plan includes a large walk-in closet and ensuite bath with a stand-up shower. The front guest suite offers a triple bay window, walk-in closet, and a full tub/shower combo. Wood flooring throughout the bedrooms, living and dining areas, with ceramic tile in the kitchen and baths. The newly updated eat-in kitchen features beautifully refinished cabinetry, a full appliance package, and ample countertop space. The expansive screened and caged lanai is lakefront and spans the full width of the home—perfect for relaxing, enjoying sunsets, and observing the turtles and ducks on the water! Additional highlights include a private 2-car garage, and a large entry courtyard with a low-maintenance xeriscape shell bedding. Community amenities include a lakefront pool and hot tub, his/her restrooms and gazebo deck area if you'd like to get out of the sun. HOA fees cover basic Dish Network streaming and internet, exterior paint, landscaping, community insurance and reserves, lawn care, and pest control. A fantastic location - just minutes to UTC Mall, SRQ Airport, downtown Sarasota, and our famous Gulf beaches. Live the relaxed Florida lifestyle and claim your personal piece of paradise in this amazing lakefront villa! All it needs is you!
Listing is courtesy of: DREAMIFY REAL ESTATE LLC (941-827-0700)
Listing Agent: Michael Grant (941-800-8585)
4085 GOLD DUST LN, SARASOTA, FL 34243
$359,000371 Days on yellowkey MLS ID: A4650212
REDUCED by $30,000 (7.7%) on 04/22/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1673 Built: 2025Monthly Fee: $199Community: Oasis At Longwood RunTownhouse
Taxes:$0
Remarks: MOVE IN READY! REDTAG SALE! Receive up to $20,000 towards closing costs, $5,000 towards upgrades and special interest rates with the use of our preferred lender - Now through Sunday, April 26th. Self-guided tour available on this quick move-in home every day from 7am-9pm. Stop by to tour on your own time. This two-story, all concrete block constructed townhome has an open concept downstairs that includes a large open kitchen, a powder room, and a large family room that overlooks a covered lanai. The second floor includes a spacious Bedroom 1 with ensuite bath, two additional bedrooms, a full bathroom, and a laundry area. This home comes with all appliances, including a stainless-steel refrigerator, built-in dishwasher, electric range, microwave, washer, and dryer. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing.
Listing is courtesy of: D.R. HORTON REALTY OF SARASOTA (941-256-7010)
Listing Agent: Sarah Bordeaux (941-367-2571)
236 DAVIS BLVD, SARASOTA, FL 34237
$699,000352 Days on yellowkey MLS ID: A4652150
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1940 Built: 1966 Tax: $6,731 (2024)Community: Ringling ParkSingle Family
Taxes:$6,731
Remarks: Three-Bedroom Pool Home with Great Potential in Ringling Park Located in Sarasota’s established Ringling Park neighborhood, this 3-bedroom, 2-bath home offers solid potential and a fantastic opportunity to make it your own. Set on a spacious pie-shaped lot, the property includes a BRAND-NEW roof, an in-ground caged pool, and ample yard space, fully fenced—perfect for outdoor living or pets. Inside, the layout features a bonus room that can serve as a home office, or flex space. The kitchen is equipped with newer appliances. There is a 1-car garage, extra storage plus a large driveway providing plenty of parking. The location of this home is a true standout—just minutes from downtown Sarasota, local parks, and schools. Whether you're looking for a primary residence, investment, or renovation project, this property offers a great foundation in a highly desirable area. This home is currently rented.
4633 OAK HILL DR #13, SARASOTA, FL 34232
$249,0003 Days on yellowkey MLS ID: A4691571
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1451 Built: 1985Monthly Fee: $559 Tax: $3,309 (2025)Community: Village Oaks Sec BSpa: NoVilla
Taxes:$3,309
Remarks: Centrally located and nestle amongst lush foliage and stately oaks this 2 bedroom 2 bath villa is ready to call your new home. Updated kitchen with newer appliances and laminate flooring are just a few of the upgrades you will find in this spacious villa. The master bath boasts a beautifully remastered walk-in-shower with optional hand held shower head as well as grab bars for handicap accessibility. The vaulted living ceilings adds to the spacious feeling of this home. The enclosed lanai offers additional living space and would be a perfect spot to set up your office. The exterior of the property has a new roof, new garage door, new gutters and is maintained by the Association. Village Oaks is an active community with tennis & pickleball courts, a lakeside pool and park. Just minutes away from downtown Sarasota, The UTC Mall, Benderson Rowing facility and many options for dining and shopping. Property is sold "As Is" please use an "As Is" contract, please provide proof of funds or pre-approval letter. Room measurements are approximates and should be verified by the buyer.
Listing Agent: Shirley Cuddy (941-321-1549)
111 S PINEAPPLE AVE #904, SARASOTA, FL 34236
$1,260,00013 Days on yellowkey MLS ID: A4689993
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1513 Built: 2019 Tax: $11,635 (2025)Community: Mark Sarasota CondoSpa: NoCondo
Taxes:$11,635
Remarks: Experience elevated urban living in this sophisticated and impeccably designed two-bedroom, two-and-a-half-bath residence with a versatile den at The Mark in the heart of Downtown Sarasota. Designed for both comfort and style, the expansive great room is framed by a striking wall of glass filling the space with natural light, offering captivating views of prestigious State Street. The home features custom-installed closet systems and Porcelain flooring throughout, complemented by blackout shades for effortless light and privacy control. The modern kitchen is a true showpiece, featuring Nolte soft-close cabinetry, quartz countertops, and a designer tile backsplash. Premium JennAir appliances—including an induction oven, dishwasher, microwave drawer, and refrigerator—are paired with under-cabinet lighting and an inviting island with seating, perfect for entertaining. Step outside to your private outdoor terrace, perfectly positioned to take in sweeping views of the Sarasota skyline and facing east—an ideal setting to enjoy breathtaking sunrises and morning coffee or afternoon cocktails with a birds-eye view of the sidewalk café scene. The generously sized owner’s suite offers a serene retreat, complete with two closets, including a spacious walk-in. The spa-inspired bathroom boasts a double vanity with quartz countertops, a private water closet with a Kohler toilet, and a walk-in shower with a seamless glass enclosure. A heated towel rack adds an extra layer of luxury. A well-appointed guest suite with its own en-suite bath provides comfort and privacy for visitors, while the den offers excellent flexibility as a home office or potential third bedroom. An elegant powder room completes this exceptional residence. Residents of The Mark enjoy premium lifestyle amenities including 24-hour concierge service, a resort-style heated saltwater pool and spa, state-of-the-art fitness center with a dedicated spin room, a club room with catering kitchen, fireplace and billiards, as well as outdoor lounging areas with fire pits, grills, and dining spaces — all just steps from the Saturday Farmers Market, Whole Foods, Bayfront Park, shopping, dining, galleries and Sarasota’s renowned cultural venues. Living in the heart of downtown Sarasota, residents are in close proximity to the waterfront, including Marina Jack and Oleary’s, outdoor art, food and music festivals, and the Bay Runner shuttle to the beach. Experience a full rounded Floridian lifestyle at The Mark.
Listing Agent: Lynn Morris, Pllc (941-400-4526)
630 CORWOOD DR, SARASOTA, FL 34234
$875,00011 Days on yellowkey MLS ID: A4690643
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1897 Built: 1963 Tax: $7,711 (2025)Community: Corwood ParkSpa: NoSingle Family
Taxes:$7,711
Remarks: Discover the perfect blend of location, lifestyle, and future potential in this beautifully updated residence in the desirable Corwood Park neighborhood. Situated on an expansive ~0.22-acre lot, this property offers a rare opportunity to enjoy move-in-ready comfort today while preserving room for tomorrow’s vision. Thoughtfully renovated, the home showcases a modern kitchen with shaker cabinetry, new countertops, new High Efficiency washer and dryer and stainless-steel appliances, complemented by updated bathrooms, new tile flooring throughout, and impact patio doors. The outdoor space is equally impressive, featuring a refreshed pool area ideal for entertaining or relaxing under the Florida sun. What truly sets this property apart is the generous lot size, flexibility and expanded living spaces, demonstrating the strong upside potential for expansion or redevelopment. Surrounded by lush tropical vegetation and mature trees, the property offers privacy and a serene setting, with ample space to add square footage, a guest house, or enhanced outdoor living features—subject to local zoning. Ideally located west of the Trail, this home is just moments from Sarasota Bay, where you can enjoy evening sunsets, and only minutes to cultural landmarks like the Ringling Museum, Sarasota Jungle Gardens, downtown Sarasota, SRQ Airport, and world-class beaches. Whether you’re seeking a primary residence, seasonal retreat, or investment with upside potential, this property delivers location, land value, and lifestyle—all in one of Sarasota’s most promising growth corridors.
Listing is courtesy of: CCI REALTY (954-667-6692)
Listing Agent: Oscar Betancourt (954-854-3959)
350 GOLDEN GATE PT #51, SARASOTA, FL 34236
$1,350,00022 Days on yellowkey MLS ID: A4689328
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1760 Built: 1969 Tax: $6,998 (2025)Community: Bay Point AptsSpa: NoCondo
Taxes:$6,998
Remarks: Refined waterfront living at the peaceful southwest corner of Golden Gate Point. This impeccably renovated corner residence captures sweeping, unobstructed views of Sarasota Bay, Bird Key, and the iconic John Ringling Bridge through walls of impact-rated PGT windows—delivering breathtaking sunsets and a true sense of coastal serenity. Designed for both elegance and ease, the open-concept living and dining spaces flow seamlessly from a sophisticated, modern kitchen featuring quartz countertops, sleek melamine cabinetry, and cork flooring. Premium stainless appliances include a JennAir induction cooktop with downdraft, Bosch dishwasher, LG refrigerator, KitchenAid trash compactor, and Whirlpool microwave/oven. A built-in desk, composite sink, and WaterPro Reverse Osmosis System for drinking water elevate everyday functionality, while a thoughtfully designed prep kitchen offers discreet, highly efficient storage for pantry items and small appliances. The primary suite is a private sanctuary, complete with a custom built-in dresser, mounted TV, designer pendant lighting, and a fully customized 13’ x 6’ walk-in closet by The Container Store. The spa-inspired bath showcases floating dual vanities, a dedicated makeup area, two appliance garages, a jetted tub/shower combination, heated towel rack, and a striking designer feature wall. The stacked washer and dryer are conveniently tucked away behind a sliding mirrored door. A versatile second bedroom with Murphy bed and closet easily transforms into a refined home office or guest retreat. Additional highlights include curated finishes throughout, including feature walls in the living room, primary suite, and primary bath, and a beautifully appointed guest bath with porcelain tile flooring and walls, floating vanity with under-cabinet lighting, and another towel warmer. Residents enjoy an intimate boutique setting with a heated bayfront pool, day dock, outdoor shower, renovated pool bath, covered assigned parking, and ample guest parking. Just moments from the dining, arts, and culture of Downtown Sarasota, the boutiques and restaurants of St. Armands Circle, and the white-sand beaches of Lido Key. A rare opportunity to own a turnkey residence in one of Sarasota’s most prestigious waterfront enclaves.
Listing Agent: Mackenzie Longueuil (941-961-4023)
3514 24TH PKWY, SARASOTA, FL 34235
$377,00012 Days on yellowkey MLS ID: A4689497
REDUCED by $10,000 (2.6%) on 04/23/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1568 Built: 1961 Tax: $1,415 (2025)Community: Kensington ParkSingle Family
Taxes:$1,415
Remarks: Beautiful pool home offering comfort, versatility, and a great location near UTC. This block construction property features 3 bedrooms, 2 bathrooms, former garage has been coverted to finished storage with full bath and wetbar. The home has been remodeled and is move-in ready with a newer roof and A/C, providing peace of mind for the next owner. Enjoy the spacious, private fenced backyard with a pool—ideal for entertaining or relaxing. With no deed restrictions, there is plenty of room for all your toys, including boats, RVs, or additional vehicles. Conveniently located near UTC, shopping, dining, and major roadways, this property offers both flexibility and lifestyle. Ready for immediate occupancy—schedule your private showing today!
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Beverly Perez (941-323-4600)
111 S PINEAPPLE AVE #806, SARASOTA, FL 34236
$1,795,00034 Days on yellowkey MLS ID: A4687850
REDUCED by $50,000 (2.7%) on 04/22/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1891 Built: 2019 Tax: $12,679 (2025)Community: Mark Sarasota CondoCondo
Taxes:$12,679
Remarks: Experience refined downtown living at Sarasota’s premier address, The Mark. This 8th-floor end unit offers 2 bedrooms plus a den, 2.5 bathrooms, and abundant natural light with a desirable south-facing terrace and additional east and west views. The thoughtfully designed floor plan features two private terraces, including a unique triangular terrace off the main living area and a second terrace off the primary suite. Interior highlights include porcelain tile and engineered hardwood flooring, a spacious walk-in closet with custom built-ins in the primary bedroom, custom built-ins in the guest bedroom, and remote-controlled shades throughout. The kitchen showcases a modern European design with glossy white upper cabinetry, wood-grain lower cabinets, a full-height backsplash, and top-of-the-line appliances. Enjoy unmatched walkability with shops, restaurants, and galleries just steps from your door, offering the ultimate downtown Sarasota lifestyle.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Amber Watson (229-392-8892)
510 N OSPREY AVE, SARASOTA, FL 34236
$947,00070 Days on yellowkey MLS ID: A4682221
REDUCED by $50,000 (5.0%) on 04/24/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1354 Built: 1954 Tax: $6,459 (2025)Community: Inwood Park First AddSingle Family
Taxes:$6,459
Remarks: Price Improvement! Located in the highly sought-after Gillespie Park neighborhood, this updated 3-bedroom, 2-bath home offers a blend of character, modern upgrades, and exceptional walkability to downtown Sarasota. Just minutes from Main Street, enjoy easy access to dining, shopping, galleries, theaters, and the Sarasota Farmers Market. Inside, polished terrazzo floors highlight the home’s mid-century charm, while the updated kitchen features granite countertops, newer appliances, and opens to a flexible sitting or dining area. The thoughtfully designed layout provides both comfort and functionality. The home includes a newer primary suite addition with a walk-in closet and en-suite bath, along with a bonus area ideal for an office, study, or sitting space, plus a dedicated laundry room. Recent improvements include updated windows, air-conditioning system, hot water heater, and washer/dryer, enhancing efficiency and move-in readiness. The private backyard features mature landscaping and irrigation, with ample space for a pool and potential for an accessory dwelling unit (ADU), subject to city approval. Property is located within the City of Sarasota’s 7-day minimum rental district, offering added flexibility for future use or investment. Conveniently located near Sarasota Bay, The Bay Park, John Ringling Bridge, and Lido Beach, this home provides easy access to waterfront amenities, downtown living, and area beaches. Property may have audio and/or video surveillance. Buyer and buyer’s agent should be aware they may be recorded.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Rex Glasson (941-587-6135)
3856 27TH PKWY, SARASOTA, FL 34235
$329,00075 Days on yellowkey MLS ID: A4682653
REDUCED by $10,000 (2.9%) on 04/28/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1014 Built: 1960 Tax: $1,218 (2025)Community: Kensington ParkSingle Family
Taxes:$1,218
Remarks: Wonderful opportunity to live in Kensington Park. This 2 bedroom 1.5 bath block home is nicely situated on a well established lot with mature Oak trees and Mature fruit trees. The kitchen has been completely redone with quartz counters, luxury vinyl flooring and solid wood cabinets. New Roof in 2020, new hot water heater 2022, updated kitchen and bath 2022, New Hvac 2023. House has been repiped in 2014 and cast iron replaced in 2023. Nice 8'x12' shed in the back.Easy access to the beach and shops.
Listing is courtesy of: SHIRLEY INTERNATIONAL REALTY (941-448-4872)
Listing Agent: David Barkema (941-284-4858)
1168 WESTWAY DR, SARASOTA, FL 34236
$3,250,00098 Days on yellowkey MLS ID: A4677843
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2858 Built: 2002Monthly Fee: $42 Tax: $28,934 (2025)Community: Lido ShoresSpa: NoSingle Family
Taxes:$28,934
Remarks: In the sought-after Lido Shores community with deeded beach access, this striking contemporary residence is a rare architectural offering designed by renowned Swiss architect Hans Ritschard. Thoughtfully updated while honoring its modernist roots, the home seamlessly blends timeless design with today’s lifestyle. At the heart of the home is a dramatic atrium, an architectural centerpiece designed for year-round enjoyment. Sixteen-foot floor-to-ceiling windows on three sides frame tranquil views of the 54ftx 18ft covered patio, the lap pool and lush palm-filled grounds, while clerestory windows introduce warm, indirect sunset light from the fourth side. A state-of-the-art climate control system ensures comfort in every season, making this space ideal for gathering, relaxing and entertaining, rain or shine. The newly renovated gourmet kitchen anchors the living spaces, featuring sleek finishes and an open-concept layout that overlooks the atrium, ideal for everyday living and hosting guests while preparing a favorite meal. The residence offers three bedrooms and three baths, along with a versatile ground-level flex space that can easily serve as an additional bedroom, home office or private gym. The lower level includes a walk-out family room with sliding glass doors that open directly to the outdoor living areas, enhancing the home’s seamless indoor-outdoor connection. A two-car garage provides ample storage, including a dedicated closet for beach gear, bikes and recreational equipment.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Kimberly Ide (401-487-6928)
2304 RINGLING BLVD #217, SARASOTA, FL 34237
$160,000108 Days on yellowkey MLS ID: A4677209
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 552 Built: 1965 Tax: $610 (2025)Community: Garden AptsSpa: NoCondo
Taxes:$610
Remarks: One or more photo(s) has been virtually staged. This is one of those places that just makes sense the minute you walk in, and it carries architectural pedigree to match. Designed by Sarasota pioneer Ruth Richmond, this residence blends clean mid-century lines with smart, livable design just minutes from downtown. Inside, you’ll find a bright, easy one-bedroom layout with luxury vinyl plank flooring throughout, an updated kitchen that feels clean and current, and a refreshed bathroom ready to enjoy from day one. No projects. No “someday” list. Just unpack and get on with living. Richmond was known for creating efficient, light-filled spaces that live larger than their square footage, and this home delivers exactly that. Location is the real flex. Less than a mile to downtown Sarasota means coffee, restaurants, work, and events are right there. Lido Beach is just 4.7 miles away, close enough for spontaneous sunset runs without living in full tourist mode. It’s a smart fit for a downtown employee who wants convenience without the downtown price tag. It also checks the boxes as an investment property with strong rental appeal, or a low-maintenance snowbird retreat you can lock and leave without a second thought. Architectural history. Modern updates. In the middle of everything. These are the ones that don’t sit around for long.
Listing Agent: Beth Helvey Pa (941-330-3600)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.