Location: Sarasota
Do Not Show Listings
3987 MACEACHEN BLVD #133, SARASOTA, FL 34233
$154,90062 Days on yellowkey MLS ID: A4688227
REDUCED by $15,000 (8.8%) on 05/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 978 Built: 1978 Tax: $1,907 (2025)Community: Tregate EastCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,907
Elementary School: Wilkinson Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Sarasota Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to 3987 Maceachen Blvd, Unit 133, an updated condo located in a desirable 55+ community in Sarasota. This 2-bedroom, 2-bathroom residence offers 978 square feet of living space with bamboo hardwood flooring throughout. The primary suite features a walk-in closet and an updated en-suite bathroom with a quartz vanity and tile walk-in shower. The guest bathroom has also been remodeled and includes a quartz vanity. The kitchen has been updated with quartz countertops, new cabinetry, a built-in sink with neck faucet, and canned recessed lighting. Enjoy the private terrace overlooking the community pool and park. The building includes elevator access for added convenience. The property is conveniently located near Publix, is approximately 6 miles to Siesta Key Beach, and 5 miles to downtown Sarasota, providing easy access to shopping, dining, and entertainment. This move-in-ready condo is suitable for full-time or seasonal living within a well-located Sarasota community.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Vincent Lamaida (941-416-5654)
9397 MIDNIGHT PASS RD #905, SARASOTA, FL 34242
$729,000225 Days on yellowkey MLS ID: A4669008
REDUCED by $20,000 (2.7%) on 05/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1348 Built: 1975 Tax: $5,944 (2025)Community: Pointe On Midnight PassSpa: YesCondo
Taxes:$5,944
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Middle School: Brookside Middle
Remarks: Also available as a seasonal rental! Welcome to 9397 Midnight Pass Rd #905 Sarasota, FL 34242 at The Pointe on Siesta Key, a fully renovated 1,348 SF, 2-bedroom, 2-bathroom luxury condo offering breathtaking Little Sarasota Bay and Intracoastal waterway views from the 9th floor. This stunning residence underwent a complete custom renovation in 2023, setting it apart from every other unit in the building. The open-concept kitchen features quartz countertops, vaulted ceilings with a bold rock-and-metal aesthetic, and a one-of-a-kind handcrafted glass-art backsplash, with bar seating connecting seamlessly to the dining and living areas, a custom layout rarely found at The Pointe. Luxury vinyl plank flooring flows throughout every room including the lanai, while wood acoustical paneling enriches both the living space and primary suite. Additional upgrades include HD-mounted televisions, a 2023 AC system, and a new LG washer and dryer, making this unit nearly turnkey and move-in ready. Step onto your private lanai, protected by hurricane-grade sliders, and take in tranquil water views of Little Sarasota Bay, where dolphins, manatees, and sailboats pass through calm Intracoastal waters daily. As a resident of The Pointe's gated five-acre community, enjoy resort-style amenities including boat docks, kayak and canoe access, a heated pool and spa, sauna, tennis and pickleball courts, BBQ gazebos, a clubhouse, and a fitness center with panoramic Intracoastal views. Located just minutes from Turtle Beach, Siesta Key Village, waterfront dining, local marinas, and coastal cafés, this property is ideal whether you're seeking a luxury Siesta Key waterfront residence, a vacation condo, or a Sarasota investment property. Negotiable furnishings available. Schedule your private showing today.
Listing is courtesy of: HARRY ROBBINS ASSOC INC (941-924-8346)
Listing Agent: Emerson Robbins (941-404-0382)
6154 MIDNIGHT PASS RD #7C, SARASOTA, FL 34242
$645,00067 Days on yellowkey MLS ID: A4687416
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 836 Built: 1966 Tax: $4,329 (2025)Community: Casa Blanca VillasCondo
Taxes:$4,329
Remarks: Positioned along the powdery white sands of Siesta Key’s renowned Crescent Beach, this villa residence within Casa Blanca Beach Resort presents an exceptional opportunity to own in one of Sarasota’s most iconic Gulf-front communities. Casa Blanca is a unique collection of individually owned villas and apartments, each thoughtfully furnished and appointed for effortless coastal living or income-producing flexibility, with minimum rental periods of just 5–7 nights depending on ownership preference. This two-bedroom residence is fully equipped with an updated kitchen and bathroom, all cookware and linens, and the conveniences of individually controlled air conditioning, cable television, and Wi-Fi, creating a seamless turnkey experience for both owners and guests. The community enhances the Gulf-front setting with a clubhouse, pool and multiple on-site laundry facilities, all designed to support easy, resort-style living. Set directly on Crescent Beach, internationally celebrated for its fine, quartz-crystal sand and consistently ranked among the top beaches in the United States, this property captures the essence of Sarasota’s coastal appeal. Ideally situated just off Stickney Point Bridge, it offers effortless access to Sarasota’s renowned dining, shopping, and cultural attractions. With Siesta Beach just steps away, this is a rare opportunity to own in a beloved beachfront destination, whether as a personal retreat, full-time residence, or high-demand investment property.
Listing Agent: Joel Schemmel (941-587-4894)
464 GOLDEN GATE PT #702, SARASOTA, FL 34236
$4,295,000235 Days on yellowkey MLS ID: A4667652
Bed: 3 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3377 Built: 2006 Tax: $51,212 (2025)Community: La BellasaraSpa: YesCondo
Taxes:$51,212
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Experience luxury waterfront living at La Bellasara on Golden Gate Point. This 7th-floor, 3-bedroom plus den, 4.5-bath residence captures breathtaking, panoramic forever views of Sarasota Bay and the glittering city skyline from every room, blending sophistication with the relaxed coastal lifestyle. A private elevator opens to a grand double-door foyer, where stone floors lead through expansive living spaces with 9–11 ft. ceilings. The main living area features rich wood built-ins and flows seamlessly into the updated gourmet kitchen—complete with custom white cabinetry, top-tier appliances, a 6-burner gas range, center island, and walk-in pantry. The open layout connects to the dining area and breakfast nook, all oriented toward the water. Step outside to the 42-ft. bayfront terrace, ideal for entertaining with its built-in summer kitchen. A separate library with custom bookcases offers a quiet retreat or optional guest space. The private primary suite features two luxurious bathrooms, dual walk-in closets, a morning bar, and terrace access for sunrise views over the bay. Two guest suites, each with ensuite baths, custom closets, and private terraces, are thoughtfully positioned for privacy. Additional highlights include a private 2-car garage with extra storage conveniently located near the elevator—offering the feel of a private home with the ease of condominium living. Community amenities include concierge services, a heated pool and spa, fitness center, theater, social and meeting rooms, and a courtesy day dock. La Bellasara is a gated, pet-friendly enclave offering luxury, comfort, and an unbeatable bayfront lifestyle. Furnishings available separately.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
1921 MONTE CARLO DR #302, SARASOTA, FL 34231
$549,000353 Days on yellowkey MLS ID: A4655742
REDUCED by $26,000 (4.5%) on 04/03/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1720 Built: 2006 Tax: $6,041 (2025)Community: Phillippi Landings ACondo
Taxes:$6,041
Remarks: INCREDIBLE VALUE - this beautifully remodeled third-floor luxury residence with water view in the gated waterfront community of Phillippi Landings is perfectly situated West of the Trail and just minutes to the world-renowned beaches of Siesta Key. Nestled along the Phillippi Creek with direct access to Sarasota Bay and just minutes to the Philippi Farmhouse market and the Landings Shopping Center with its vast array of dining and shopping options. This 2 bedroom plus den, 2 bath condo offers the ideal blend of privacy, convenience, and resort-style living. NEW 2026 AC! From the moment you enter via direct elevator access to your private foyer entrance, you are welcomed by an open and airy floor plan, porcelain tile flooring, and an inviting coastal aesthetic. The beautifully updated kitchen features granite countertops, stainless appliances, and rich wood cabinetry, offering both style and function for everyday living and entertaining. Step into the spacious living area that opens to a private covered and screened balcony with peaceful water view, ideal for enjoying morning coffee or a glass of wine at sunset. The split-bedroom layout offers exceptional privacy, with two generously sized bedroom suites. The primary suite is a true retreat, offering tranquil water view, two large walk-in closets, and a spa-style bath with a jetted soaking tub, custom walk-in shower, and private water closet. A flexible bonus space off the main living area provides the perfect nook for a home office, den, reading lounge, or secondary dining area. Impact doors and windows throughout. Beautiful wood plantation shutters. Enjoy the convenience of under-building assigned parking and a private storage unit. This home is move-in ready and ideal as a primary residence, seasonal escape, or investment opportunity. A boat slip may be available to purchase separately. Life at Phillippi Landings is exceptional - the community is 10 acres and offers a resort-style heated pool and spa, a well-equipped fitness center, clubhouse, and an expansive waterfront promenade perfect for evening strolls beneath swaying palms. For boating and nature enthusiasts, the community provides kayak launch access and private storage racks—an invitation to explore the peaceful waterways of Phillippi Creek and beyond. The lush, manicured grounds and tropical landscaping create a tranquil, private atmosphere while placing you just minutes from Southside Village, downtown Sarasota, and the vibrant shopping and dining of UTC Mall. This exceptional location, paired with a refined, low-maintenance lifestyle, offers the best of coastal Florida living.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lenore Treiman (941-356-9642)
6650 SCHOONER BAY CIR #6650, SARASOTA, FL 34231
$439,00092 Days on yellowkey MLS ID: A4683877
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1206 Built: 1983Monthly Fee: $850 Tax: $5,462 (2025)Community: Schooner BayCondo
Taxes:$5,462
Elementary School: Gulf Gate Elementary
Remarks: Salt Water Canal Front - West of the Trail - Walk or Bike to Siesta Key Beach... Experience the best of coastal living in this sun-filled, spacious 2-bedroom, 2-bath residence nestled within the highly sought-after, gated boating community of Schooner Bay—just minutes from Siesta Key. Gentle coastal breezes flow through the home, while the expansive screened lanai offers an inviting setting for morning coffee or evening cocktails at sunset. Priced to allow Buyer to fully remodel to their desires without concerns of over investing.. This exceptional waterfront property includes a rare deeded boat slip.. with water and electric, providing direct access to the bay with no bridges—an ideal arrangement for boating enthusiasts. A private 1-car garage adds convenience and security. Inside, the thoughtfully designed split floor plan offers generous living spaces, in-unit laundry, and outstanding flexibility for comfortable everyday living or seasonal use. The primary suite features a spacious en-suite bath and private access to the lanai, creating a serene retreat. Notably, the residence remained unaffected by the 2024 storms, with no water intrusion or damage, offering additional peace of mind. Residents of Schooner Bay enjoy access to a heated community pool and clubhouse, all in a prime location near world-renowned beaches, shopping, dining, healthcare, and downtown Sarasota. The HOA provides a truly maintenance-free lifestyle, covering roof, sidewalks, gutters, flood insurance, and landscaping. An exceptional opportunity to personalize and enhance a waterfront property in a premier location—this is coastal living at its finest. *Property is currently located in FEMA Flood Zone X according to available public records; Buyer to independently verify.
Listing is courtesy of: SHOWTIME REALTY (941-822-0890)
Listing Agent: Robert D. Bevington (412-671-3142)
101 WHISPERING SANDS DR #107, SARASOTA, FL 34242
$475,000180 Days on yellowkey MLS ID: A4674069
REDUCED by $20,000 (4.0%) on 05/04/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1271 Built: 1969 Tax: $5,864 (2024)Community: Whispering SandsCondo
Taxes:$5,864
Tax Year: 2024
Remarks: One or more photo(s) has been virtually staged. PRICE IMPROVEMENT! Welcome to affordable GULF FRONT living! This is the BEST PRICED CONDO in Whispering Sands. The sellers are also willing to offer a $60,000 SELLER CREDIT with an acceptable offer, to offset any future improvements or assessments. This recently updated, 2 bed/2 bath, DOUBLE LANAI CORNER unit is nestled in the southwest corner of the popular Tropic View building, the Whispering Sands midrise closest to the Gulf and 800' of your own private beach! The freshly painted interior features NEW luxury vinyl plank flooring, NEW interior doors, and NEW overhead designer lighting and fans. Four sets of floor-to-ceiling sliders open from the living areas and bedrooms into TWO separate 24’ glassed and screened lanais – complete with epoxy flooring and NEW ceiling fans to capture the coastal breezes. After a full day at the beach, meal prep is easy in your partially open kitchen featuring NEW granite countertops, farmhouse style stainless sink, and NEW 2025 Whirlpool and GE stainless appliances. The spacious primary bedroom includes a nice walk-in closet and an ensuite bath, while the generous second bedroom comfortably accommodates up to two queen beds and boasts a full wall of closet space. Both updated bathrooms feature NEW cabinets, vanities, & fixtures, with glassed walk-in showers and recessed lighting. Brand NEW 2026 HVAC system and 2025 water heater. The unit also comes with its own assigned storage locker located just across the hall, ideal for storing all of your beach essentials. Conveniently located next door to the colorful shops and restaurants of Siesta Key Village, Whispering Sands is a premiere 55+ Gulf front property offering two heated pools, beachside Tiki Hut and gas grills, shuffleboard, canoe/kayak storage, and 800' of PRIVATE quartz sand beach. The clubhouse is currently undergoing complete remodeling. Upon completion in 2026, it will include a full catering kitchen, fitness rooms, large screen TV, and an elegant space for community wide or private social events. New landscaping plan for the building and throughout the entire 25-acre property is currently underway. Attractively priced below market, this unit represents a great investment. Don’t miss this opportunity to experience the ease of island living at Whispering Sands!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Harriet Stopher (404-316-8944)
1650 PINE TREE LN #103, SARASOTA, FL 34236
$309,90025 Days on yellowkey MLS ID: A4692661
REDUCED by $10,000 (3.1%) on 05/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 940 Built: 1974 Tax: $2,729 (2025)Community: Bayou House AptsCondo
Taxes:$2,729
Remarks: BREATHTAKING BAYOU HOUSE! Positioned along the peaceful waters of Hudson Bayou, this beautifully updated FIRST-FLOOR residence offers a rare blend of waterfront serenity and walkable proximity to the very best of Downtown Sarasota. From the moment you step inside, the tone is set — a clean, open layout enhanced by tasteful finishes and a natural flow that makes everyday living feel effortless. The kitchen serves as the heart of the home, featuring rich cabinetry, sleek QUARTZ countertops, and modern updates that balance both style and functionality. Thoughtfully designed with a SPLIT BEDROOM FLOOR PLAN, the layout provides a sense of privacy and separation — ideal for hosting guests or creating comfortable, independent living spaces within the home. Updated bathrooms, refined flooring, and contemporary lighting carry a cohesive feel throughout, delivering a move-in-ready environment for even the most discerning buyer. Step beyond the living space to your PRIVATE SCREENED LANAI, where one can sit sipping on a cup of their favorite brew whilst taking in the tranquil waterfront setting and serene birdsong. With direct GULF ACCESS via Hudson Bayou, this is more than just a view — it’s a lifestyle. Launch a kayak, enjoy the natural surroundings, or simply unwind as the water moves gently past your backyard. A BRAND-NEW TRANE A/C (2024) ensures year-round comfort and efficiency, adding yet another layer of confidence for the next owner. All of this, just minutes from Downtown Sarasota, where you’ll find TOP-RATED RESTAURANTS, boutique shopping, art galleries, Marina Jack, Selby Gardens, and the vibrant cultural energy that makes this area so desirable — all while returning home to your own quiet, waterfront retreat. This is the kind of opportunity that rarely presents itself — WATERFRONT, FIRST-FLOOR, MOVE-IN READY, and perfectly positioned. DO NOT ALLOW THIS RARE WATERFRONT OPPORTUNITY TO SLIP THROUGH YOUR GRASP… CALL TODAY TO SCHEDULE YOUR PRIVATE SHOWING!!!
Listing is courtesy of: KW SUNCOAST (941-792-2000)
Listing Agent: Matthew Sharp, Pa (813-629-7094)
1617 BROOKHOUSE DR #256, SARASOTA, FL 34231
$214,900146 Days on yellowkey MLS ID: A4676511
1 Days Off yellowkey (back on 5/29/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1245 Built: 1980 Tax: $3,218 (2024)Community: Pelican Cove XviCondo
Taxes:$3,218
Remarks: Under contract-accepting backup offers. GREAT NEW PRICE! This is your chance to own a piece of paradise in one of Sarasota's most sought-after waterfront communities-- Pelican Cove! This 2-bedroom, 2-bathroom condo offers a unique dynamic floorplan which allows you to easily make the most of the space to suit your needs. By means of an accordion partition, the living room can be expanded or closed off to form the 2nd bedroom. This allows occasional guests complete privacy with an ensuite bath and come outfitted with built-in cabinetry, including a Murphy bed for the ultimate in flexibility. Enjoy views of a tranquil pond with fountain from the very private glass-enclosed lanai, which spans the living area as well as the 2nd bedroom. Ideally located along Little Sarasota Bay, Pelican Cove is an exceptional 75-acre community with miles of tropical trails and walkways, an 86-slip marina with direct access to the Intercoastal Waterway, and a bird sanctuary. Additional amenities include 3 clubhouses, 6 heated pools, tennis and pickleball court, a firness center, and a dog run. "Pelican Cove University" offers a range of classes, lectures, and clubs, using studio space including an art studio, photography studio, and woodworking shop. Excellent shopping and dining options are within a 5-minute drive. 20 minutes to the myriad cultural options in downtown Sarasota. Just around the corner from Sarasota Square, now under development and slated to premiere in 2026 with new shopping, dining, and entertainment options.
Listing is courtesy of: MOUNT VERNON PROPERTY MGMT INC (941-957-4663)
Listing Agent: Jennifer Herman (941-957-4663)
4244 MADEIRA CT #3316, SARASOTA, FL 34233
$235,00083 Days on yellowkey MLS ID: A4684792
0 Days Off yellowkey (back on 5/29/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1063 Built: 1989Monthly Fee: $458 Tax: $2,709 (2025)Community: Casa Del Sol Sec ViiSpa: NoCondo
Taxes:$2,709
Elementary School: Ashton Elementary
Remarks: Under contract-accepting backup offers. Serene lake views create a peaceful setting for this beautifully maintained and thoughtfully updated second floor, TURNKEY FURNISHED, two bedroom, two bath residence in the welcoming community of Casa Del Sol. As an end residence with only one shared wall, it offers added privacy, while the elevated location provides a sweeping view of the tranquil lake and surrounding landscape. Vaulted ceilings and mirrored walls enhance the spacious feel of the great room plan and eat in kitchen. Both bedrooms feature walk in closets, and the primary suite enjoys lake views, private lanai access, and an en suite bath. Sliding glass doors open to a covered and screened lanai, perfect for relaxing and enjoying the scenery. Additional conveniences include ceiling fans, private laundry with washer and dryer included, and assigned covered parking. Notable UPGRADES include a beautifully UPDATED kitchen and bathrooms with new cabinets and granite counters, raised kitchen ceiling, hurricane rated sliding glass doors on the lanai, flooring, a full RE-PIPE completed in 2020, and an A/C system replaced in 2017 with warranty coverage through October 5, 2027. This section of Casa del Sol overlooks the community clubhouse and year round heated pool. Casa Del Sol is not age restricted and is known for its low association fees, manicured grounds, and active social atmosphere. Amenities include a clubhouse with kitchen, game room, exercise facilities, shuffleboard, tennis courts with pickleball, bocce ball and a heated pool. Ideally located in central Sarasota, the community sits across from numerous shopping and dining options and near the local bus route and Doctors Hospital. Cattlemen Road provides quick access to Bee Ridge Road, Proctor Road, Fruitville Road, and I 75, with championship golf, downtown Sarasota, and the area’s renowned white sand beaches just a short drive away.
Listing Agent: Jackie De Manio Eberley (201-233-1959)
9200 MIDNIGHT PASS RD #25, SARASOTA, FL 34242
$429,00028 Days on yellowkey MLS ID: A4692488
REDUCED by $20,000 (4.5%) on 05/26/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 906 Built: 1972 Tax: $4,028 (2025)Community: Inlet AptsCondo
Taxes:$4,028
Remarks: Introducing Inlet Apartments - Siesta Key, a charming, quaint coastal retreat for a tropical vacation or a beach getaway. This second-floor, one-bedroom, one-bath is quiet and peaceful on the Blind Pass Lagoon at far south end of Siesta Key and just beyond your sliding glass doors. You will be instantly captivated by views of paddleboarders and kayaks going by, plus a heated swimming pool and a partial view of the Gulf. With 906 square feet, this residence is sold turnkey furnished, blending modern sophistication with relaxed coastal living. Contemporary new kitchen with new appliances, white quartz countertops, an oversized island, and crafted for effortless everyday living. The open-concept layout flows through the dining room, with a queen-size Murphy bed for extra guests, and living spaces, enhanced by luxury vinyl wood flooring and modern compact ceiling fans that adjust with touch of a button. Wake up to enchanting lagoon views in the tranquil primary suite, and beautifully updated bath. Go outside to a spectacular 200-square-foot screened lanai with pull-down shades for privacy, ideal for morning espresso, sunset cocktails or simply soaking in Siesta Key’s year-round beauty. There are convenient elevators, laundry facilities and assigned parking for each unit. HVAC in 2021, water heater in 2022. Life at Inlet boating amenities included private boat dockage for sailboats and powerboats up to 26 feet (first-come, first-serve basis). The Blind Pass Lagoon leads into Sarasota Bay and onto the Gulf. There are fishing, kayak storage and launch, waterfront pool, all just minutes from Turtle Beach and a short trolley ride to Crescent Key Village. This is more than a condominium at the beach, it’s a one-of-kind opportunity to own a piece of Siesta Key.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Lisa Gullick (941-364-4000)
9610 CLUB SOUTH CIR ## 4207, SARASOTA, FL 34238
$289,90043 Days on yellowkey MLS ID: A4690465
0 Days Off yellowkey (back on 4/27/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1106 Built: 1995Monthly Fee: $571 Tax: $2,887 (2025)Community: Stoneybrook Clubside South 1Condo
Taxes:$2,887
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Middle School: Laurel Nokomis Middle
Remarks: Under contract-accepting backup offers. Stoneybrook Golf & Country Club is one of the area’s most popular private clubs. Residents of Clubside South can take advantage of their own tennis and pickle ball courts, swimming pool & outdoor kitchen area, along with a carport and storage unit for each condo. Membership in the Country Club is mandatory and provides an exceptional dining experience; full-service cocktail lounge; heated pool & spa, tennis, pickle ball, fitness center, bocce ball, putting greens, driving range, pro shop and the beautifully re-designed 18-hole championship golf course. There’s a full calendar of social activities such as MahJongg, bridge, yoga, line dancing all year round. This 2BR condo is on the second floor, adjacent to the elevator. Nicely updated, it will be sold turnkey-furnished, clean & ready for quick occupancy. Conveniently located just a few miles from the arts, culture and dining in downtown Sarasota, and minutes away from the white sands of world-famous Siesta Key Beach. It’s the perfect spot for vacations, or full-time resort living. A flexible leasing policy also makes it a good investment opportunity.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-556-2150)
Listing Agent: Jane Tice (561-676-6544)
435 S GULFSTREAM AVE #1004, SARASOTA, FL 34236
$895,000210 Days on yellowkey MLS ID: A4670726
REDUCED by $55,000 (5.8%) on 05/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1829 Built: 1972 Tax: $10,813 (2025)Community: Regency HouseSpa: NoCondo
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)
5600 BEACH WAY DR #315, SARASOTA, FL 34242
$770,000356 Days on yellowkey MLS ID: A4655560
REDUCED by $10,000 (1.3%) on 05/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1259 Built: 1970 Tax: $7,099 (2024)Community: Beachway AptsCondo
Taxes:$7,099
Remarks: Are you ready to create your lifestyle in the sun, steps away from the quartz crystal white powdery sands and warm Gulf waters of the award-winning Siesta Key Beach? This wonderfully located turn-key, furnished condo end unit is oh so unique on the top floor with views of the beautiful beach and Gulf waters, a rare, remodeled find on the spectacular Gulf coasts of Florida! The rental income is excellent! This recently, completely remodeled from ceiling to floor, wall to wall, unit has 2 bedrooms, 2 bathrooms, hard flooring throughout, a sprawling island, quartz countertops, impact windows and sliders, AND has a spacious balcony, ready for you to relax and enjoy. This unit transfers with $50,000 in furnishings and furniture. This is a perfect place for you to have your dream of a beach life come to reality, with the potential of using it to generate income with monthly rentals. This amazing mid-rise condominium community offers a heated community pool, outside grills, a clubroom with a kitchen, plenty of guest parking and a laundry room on each floor. Recent improvements include newer roofs 2020, a newer elevator 2019, re-plumbed stacks 2018, refreshed landscaping 2020, and new vinyl fencing 2021. The quarterly fee includes access to the heated community pool, basic cable, water/sewer, pest control, weekend on-site maintenance person, and community insurance. Enjoy convenient access to Siesta Key Beach and to Siesta Key Village shops and restaurants with the free trolley service that stops right in front of the Beach Way community, or, walk, orrrrr take a bike cruise to many nearby shops and restaurants… You are not only buying a beach property, you are buying a lifestyle in the beautiful Southwest Florida Sun. This unit can be your own sanctuary escape and your retirement investment... Come see, come sigh and make this Siesta Key lifestyle in the Sun your own.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Karie Backman (941-404-8389)
631 N ORANGE AVE #208, SARASOTA, FL 34236
$309,900206 Days on yellowkey MLS ID: A4671326
REDUCED by $20,000 (6.1%) on 05/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 784 Built: 1982 Tax: $2,508 (2024)Community: Mentone CourtSpa: NoCondo
Taxes:$2,508
Elementary School: None
High School: None
Middle School: None
Remarks: One or more photo(s) has been virtually staged. Exceptional downtown Sarasota value in the heart of the Rosemary District. One of only a few two-bedroom, two-bath residences currently available under $350,000 in the entire downtown Sarasota market, this beautifully updated second-floor corner residence at Mentone Court offers an increasingly rare opportunity to enjoy walkable city living with low ownership costs, covered parking, and immediate access to Sarasota’s dining, shopping, and cultural attractions. Located within the charming Mentone Court community of just 16 residences, this elevated complex sits above the flood plain and includes assigned covered parking for Unit #208. The professionally managed association offers remarkably low HOA fees that include master insurance on the building, water, sewer, trash, landscaping, exterior maintenance, and reserve funding—providing exceptional value and peace of mind. The community is fully funded with no planned special assessments and is exempt from milestone inspection requirements due to its low-rise construction. Inside, the bright and thoughtfully designed layout feels open and spacious with high ceilings, large-format porcelain tile flooring, recessed lighting, and five closets for ample storage. Tropical-inspired paint tones, plantation shutters, and updated finishes create a clean, contemporary atmosphere throughout. The kitchen features refinished solid-wood cabinetry, granite countertops, under-cabinet lighting, and a striking pearlescent subway tile backsplash. Brand-new appliances—including an induction range, dishwasher, and refrigerator—have never been used, while a newer HVAC system and four Hunter remote-control ceiling fans enhance efficiency and comfort. Both bathrooms have been updated, offering a pristine cast-iron tub in one bath and an oversized walk-in shower with classic white subway tile in the other. The spacious primary bedroom easily accommodates a king-sized bed and features a California-style walk-in closet. A stacked washer and dryer are also included for added convenience. One of the residence’s standout features is the oversized screened lanai, accessed through a 12-foot sliding glass door and protected by a motorized Kevlar storm and sunshade system rated for Category 5 hurricane protection. Complete with battery backup and MagnaTrack technology, the screen also functions as a sunshade for year-round outdoor enjoyment. Mentone Court enjoys a “Walker’s Paradise” location with a walkability score of 92. Citrus Square—with multiple restaurants offering outdoor dining—is located less than a block away, while Main Street’s cafés, boutiques, Whole Foods, waterfront parks, and downtown Sarasota’s cultural attractions are all within easy walking distance. Residents also enjoy close proximity to Payne Park and the Legacy Trail, while nearby Bay Runner trolley access offers convenient transportation to St. Armands Circle, Lido Beach, and South Lido Park. Whether you are searching for a seasonal retreat, investment property, downtown pied-à-terre, or full-time residence, Unit #208 offers an exceptional opportunity to enjoy affordable downtown Sarasota living with easy beach access and outstanding walkability.
Listing Agent: Roger Pettingell (941-387-1840)
631 N ORANGE AVE #107, SARASOTA, FL 34236
$339,900314 Days on yellowkey MLS ID: A4659021
REDUCED by $20,000 (5.6%) on 05/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 784 Built: 1982 Tax: $2,713 (2024)Community: Mentone CourtCondo
Taxes:$2,713
Remarks: Downtown Sarasota living becomes exceptionally attainable with this beautifully renovated first-floor residence in the heart of the Rosemary District. One of only a handful of two-bedroom, two-bath residences currently available under $400,000 in the downtown Sarasota market, this move-in-ready home offers an unmatched combination of walkability, modern updates, low ownership costs, and immediate access to Sarasota’s vibrant urban lifestyle. Located within the charming Mentone Court community of just 16 residences, this beautifully updated unit sits above the flood plain and includes assigned covered parking only steps from the front door. Positioned within a “Walker’s Paradise” location, the residence is just a five-minute stroll to Main Street’s dining, boutiques, and cafés, a few blocks from Whole Foods, and moments from the Rosemary District’s growing collection of restaurants and outdoor gathering spaces. Citrus Square—located less than a block away—offers additional dining options and convenient access to the Bay Runner trolley and public scooter transportation for effortless connectivity throughout downtown Sarasota and the beaches. Inside, the residence has been extensively renovated and thoughtfully designed with a clean, contemporary aesthetic. High ceilings, porcelain tile flooring, 5-inch baseboards, plantation shutters, and four closets create a bright and spacious atmosphere throughout the more than 1,000-square-foot layout. The open-concept kitchen features quartz countertops, handcrafted Moroccan Zellige tile backsplash and island accents, solid hickory dovetailed cabinetry, and new Samsung smart Wi-Fi appliances including an induction range and quiet dishwasher. Both bathrooms have been beautifully reimagined with designer tile, Kohler Awaken fixtures, Choreograph shower systems, and premium glass enclosures, while a new LG heat pump washer and dryer adds everyday convenience. The residence is being offered furnished, including most furnishings, artwork, and a 75-inch Frame television, creating an ideal turnkey downtown residence, investment property, or seasonal pied-à-terre. One of the home’s standout features is the oversized private lanai with storage closet, opening directly to a tranquil green space and private gated access toward Citrus Square. A motorized Kevlar storm and sunshade system rated for Category 5 hurricane protection enhances both security and year-round usability. Mentone Court offers exceptional value with low HOA fees that include master insurance on the structure, water, sewer, trash, landscaping, exterior maintenance, and reserve funding. The professionally managed association is fully funded with no planned special assessments. The community is exempt from milestone inspection requirements due to its low-rise construction and has never experienced storm damage. Perfectly positioned near Payne Park and the Legacy Trail, the residence also offers convenient access to St. Armands Circle, Lido Beach, Longboat Key, Sarasota-Bradenton International Airport, and downtown Sarasota’s renowned cultural attractions including theaters, galleries, waterfront parks, and fine dining. Stylish, low-maintenance, and exceptionally walkable, this downtown Sarasota residence delivers an outstanding opportunity to enjoy elegant city living with easy beach access.
777 BEACH RD #1B, SARASOTA, FL 34242
$649,995405 Days on yellowkey MLS ID: A4649455
0 Days Off yellowkey (back on 4/11/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1174 Built: 1970Monthly Fee: $1,098 Tax: $8,125 (2024)Community: Crescent Royale 3Spa: NoCondo
Taxes:$8,125
Remarks: PRICED TO SELL! 100K PRICE IMPROVEMENT!! THE SEASON IS HERE! Don't miss your chance to secure a great investment with this consistently rented condo. Welcome home to the GOOD LIFE in Siesta Key Beach! This turn-key condo is ready for you to experience the epitome of beachside living year 'round as you awaken to the scent of salt air and the sound of waves rolling in, all from the comfort of your living room! This fully furnished, OPEN FLOOR PLAN, two-bedroom, two-bath condominium is positioned in the sought-after community of Crescent Royale directly across from Siesta Key’s world-renowned powdery sand beaches. Designed for those who value luxury and laid-back coastal elegance combined with smart investment potential, this prime, first-floor, turnkey condominium offers the ideal combination of luxury, convenience and relaxation. There is no need to take the stairs or search for beach parking when you live steps from the beach with an assigned parking space. Wake to panoramic views of turquoise water and unwind on your private lanai with stunning gulf sunsets. Inside, you’ll be greeted by bright, light-filled spaces with floor-to-ceiling sliders that invite in ocean breezes. The tastefully renovated home has newly installed white oak (LVP) floors throughout. A stylish kitchen complete with granite countertops, newer appliances, and a breakfast/wine bar that flows into the dining and living area creates a space for hosting with ease. Each bedroom is a serene retreat complete with a walk-in closet and a sophisticated en-suite bath, ideal for guests and owners alike. Crescent Royale pampers their residents and guests with resort-style amenities including a sparkling heated pool, fully equipped fitness center, game room, shuffleboard court, and a picnic/barbecue area. Just minutes away, Sarasota adds a cultural heartbeat with art galleries, theaters and gourmet dining. The pace here is relaxed but vibrant! Farmer’s markets, waterfront cafes and year-round sunshine create the ideal blend of sophisticated living and coastal charm. Living near Siesta Key and Sarasota means every day feels like a vacation, and every moment feels like home. Whether you're looking for a personal retreat, a seasonal escape or an income-generating asset, this property delivers because it works while you relax. Beyond its beauty, this residence is a savvy investment, offering strong rental income potential, friendly leasing policies and on-site management, creating a rare opportunity for a passive income stream in one of Florida’s most desirable beach communities. No pets or smoking allowed in this community! Location, luxury and income potential! Live the dream, earn while you’re away and invest in a lifestyle that pays you back. This condominium delivers the lifestyle you’ve been dreaming of, just across from Siesta Key Beach so don’t miss this rare chance to own a slice of Siesta Key’s desirable beachfront real estate, with income potential to match. Call us today to schedule your private showing and begin living the Florida Lifestyle you have dreamed of.
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-907-9541)
Listing Agent: Trish Chandler (941-306-9533)
2050 BENJAMIN FRANKLIN DR #B704, SARASOTA, FL 34236
$2,650,000194 Days on yellowkey MLS ID: A4672363
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2936 Built: 2005 Tax: $21,527 (2024)Community: Orchid Beach Club ResidencesSpa: YesCondo
Taxes:$21,527
Remarks: Turnkey furnished executive residence set high on the seventh floor of Orchid Beach Club, this Lido Key beachfront condominium captures sweeping Gulf, bay, and downtown Sarasota views from the moment of arrival. Designed for elevated coastal living, the nearly 3,000-square-foot layout offers three bedrooms, three full baths, private elevator access, and multiple terraces that create a seamless indoor-outdoor lifestyle. A residents-only elevator opens directly into a private lobby, where double iron filigree doors introduce a refined interior filled with natural light. High cove ceilings with inset lighting, custom millwork, wood paneling, motorized window treatments, and thoughtfully updated finishes establish a polished, modern aesthetic. Walls of impact glass frame unobstructed water and city vistas, enhancing every living space. The gourmet kitchen blends clean design with functionality, featuring quartz countertops, sleek cabinetry, center island with seating, breakfast bar, and premium Bosch and Dacor appliances, including a six-burner gas range and warming drawer. The kitchen flows effortlessly into the great room and dining area, creating an ideal setting for both entertaining and everyday living. The Gulf-front primary suite offers a private retreat with terrace access, dual walk-in closets, and a renovated bath featuring marble-inspired finishes, dual vanities, soaking tub, and walk-in shower. Two guest suites are positioned in a split layout for privacy—one with terrace access and the other with its own private balcony—providing comfortable accommodations for visitors. Three terraces extend the living experience outdoors. The expansive bay-facing terrace features a full summer kitchen with a new (2024) built-in gas grill, generous dining area, and ample seating space for sunset entertaining. A Gulf-facing terrace is shared by the primary suite and third bedroom, while the second guest suite enjoys its own secluded balcony. Orchid Beach Club is an exclusive Gulf-front community of just 54 residences, offering a full-service lifestyle with 24-hour gated entry, concierge services, and a recently updated clubhouse featuring a social room, catering kitchen, library, billiards, and lounge. The wellness amenities include a fitness center, sauna, spa room, and massage services. Outdoors, the Gulf-side pool and spa are surrounded by a spacious sun deck, with direct access to Lido Beach’s soft sand and turquoise waters. Ideally located near St. Armands Circle, Longboat Key, and downtown Sarasota, residents enjoy close proximity to fine dining, boutique shopping, marinas, and renowned cultural venues including the Van Wezel Performing Arts Hall, Sarasota Opera House, and The Ringling Museum. This turnkey furnished executive residence offers a rare opportunity to experience beachfront living with exceptional views, privacy, and convenience on Lido Key.
5955 MIDNIGHT PASS RD #4E, SARASOTA, FL 34242
$412,000114 Days on yellowkey MLS ID: A4681682
1 Days Off yellowkey (back on 4/28/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 522 Built: 1978 Tax: $3,369 (2025)Community: Contntls Sea Club 2 P1Condo
Taxes:$3,369
Remarks: Under contract-accepting backup offers. *Seller Financing Available* An exceptional opportunity awaits in Sea Club II, one of the limited Siesta Key communities permitting nightly rentals—positioning this residence as a prime option for short-term revenue potential. This ground-level one-bedroom, one-bath condo comes fully furnished and has a proven record of performance, grossing over $50,000 annually in rental income. Designed for effortless use by owners and guests alike, the unit is ready for immediate occupancy or continued income production. Sea Club II offers a resort-style setting along the Intracoastal Waterway. Residents and guests enjoy a recently updated pool area accented by brick pavers, a tiki-style pavilion, and grilling stations, creating an inviting space for leisure and gatherings. Boating and fishing enthusiasts will appreciate the community fishing pier added in 2021 and convenient access to the community boat basin. What truly distinguishes this property is its deeded beach access just a short walk away—delivering the rare advantage of Intracoastal waterfront living paired with direct access to the world-famous sands of Siesta Key Beach. Whether used as a personal island retreat or a high-demand vacation rental, this condo offers flexibility, location, and income potential in one compelling package.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Taylor Thompson (941-928-2372)
9397 MIDNIGHT PASS RD #603, SARASOTA, FL 34242
$349,000134 Days on yellowkey MLS ID: A4678849
0 Days Off yellowkey (back on 5/17/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 778 Built: 1975 Tax: $4,215 (2025)Community: Pointe On Midnight PassCondo
Taxes:$4,215
Remarks: Under contract-accepting backup offers. Experience unparalleled island living at The Pointe, a gated waterfront community at Siesta Key’s southernmost tip. This beautifully updated 1-bedroom, 1-bathroom condo boasts breathtaking bay and Intracoastal views, offering the perfect blend of tranquility and modern convenience. The open-concept layout is enhanced by sleek flooring and a contemporary kitchen with updated appliances and stylish finishes. A spacious lanai, accessible from the living area and bedroom, provides the ideal spot for morning coffee or evening relaxation while soaking in picturesque water views. Ample storage and in-unit laundry add convenience to this thoughtfully designed space. The Pointe offers an array of resort-style amenities, including a heated pool, spa, sauna, and fitness center. Enjoy friendly matches on the lighted tennis and pickleball courts, or take advantage of private boat docks and a dedicated kayak launch for easy access to the surrounding waters. Residents enjoy just a short walk to Turtle Beach. Boater? Dock access is only $100/month on a first come, first serve basis. A great value for boat owners, The clubhouse and outdoor pavilion with BBQ grills make entertaining effortless. One of the most exciting aspects of this location is the recent reopening of Midnight Pass, restoring the natural water flow between the Gulf of Mexico and the Intracoastal Waterway. This revitalization has improved water clarity and marine life, making this area even more desirable for boating, fishing, and water sports enthusiasts. Just minutes away, Turtle Beach offers pristine sands and tranquil Gulf waters, while nearby Siesta Key Village provides a variety of dining, shopping, and entertainment options. Whether seeking adventure or relaxation, this vibrant community has it all. Furnishings optional, this stunning residence is move-in ready. Don’t miss the opportunity to own a piece of paradise in one of Siesta Key’s most sought-after waterfront communities. Experience the beauty, convenience, and coastal charm of The Pointe—your perfect island retreat awaits! SEE VIRTUAL TOUR LINK
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Tracy Srodes (813-267-1312)
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