Location: Sarasota
Do Not Show Listings
4338 MADEIRA CT #3346, SARASOTA, FL 34233
$190,00037 Days on yellowkey MLS ID: A4692389
0 Days Off yellowkey (back on 6/12/2026)
REDUCED by $5,000 (2.6%) on 06/07/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1003 Built: 1988 Tax: $2,516 (2025)Community: Casa Del Sol Sec ICondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,516
Elementary School: Ashton Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Sarasota Middle
Remarks: Under contract-accepting backup offers. Enjoy peaceful lake views from this move-in ready 2-bedroom, 2-bath condo—perfect for full-time living or a seasonal retreat. Located on the second floor, you’ll love the cathedral ceilings and the added privacy of having no one above, creating a bright and airy feel throughout. Gently used by part-time owners, this thoughtfully cared for condo offers an ideal Sarasota lifestyle with easy access to beaches, shopping, dining, and more. Recent updates include a 2024 HVAC system and hot water heater, along with newer appliances for added peace of mind. Some furnishings are available for convenience, making this an easy transition whether you’re looking for a primary residence or a “lock-and-leave” getaway. Low condo fees and an active community at Casa Del Sol complete the package—offering the perfect blend of comfort, location, and value.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Janice Melzer Langa (941-404-0802)
8755 OLDE HICKORY AVE #7101, SARASOTA, FL 34238
$245,00038 Days on yellowkey MLS ID: A4692392
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1314 Built: 1996Monthly Fee: $627 Tax: $1,758 (2025)Community: Stoneybrook Terrace 1Condo
Taxes:$1,758
Elementary School: None
High School: None
Middle School: None
Remarks: EXCELLENT VALUE and MOVE IN READY! Don't miss this stunning GROUND FLOOR 2-bedroom, 2-bath CORNER unit condo at the desirable Terraces at Stoneybrook Golf & Country Club. Enjoy breathtaking SUNRISE VIEWS from your lanai overlooking the FAIRWAY ON THE 8th HOLE. This condo offers PRIVACY AND ENJOYMENT since there are no other buildings across the fairway. As a corner unit, you have LARGER primary and guest bedroom suites filled with light from EXTRA WINDOWS. Renovated with elegant matching TILES THROUGHOUT, the kitchen was also updated with wooden block counters, very easy to maintain. Sold fully furnished and move-in-ready; life is good here. You have a laundry inside your condo and your car port as well as your storage unit are just outside the condo for your convenience. The Terraces have their own resort style pool as well as a rapid surface tennis/Pickleball court and a grilling area looking over the pond, preserve and golf course. You are walking distance to the Stoneybrook Golf & Country Club famous for its indoor & outdoor dining and its exceptional amenities which include a challenging Arthur Hills and Kipp Schulties designed golf course (renovated in 2024) and Har- Tru tennis courts. Other amenities include a well-equipped fitness center, heated swimming pool, and bocce ball courts. Adjacent to the scenic Legacy Trail for biking and walking and close to a plethora of shopping and dining, residents enjoy resort-style amenities just minutes away from Siesta Key Beach, ranked #1 in the US and # 4 in the world by TripAdvisor.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Melanie Albaric (941-233-0957)
6140 MIDNIGHT PASS RD #904, SARASOTA, FL 34242
$2,350,00065 Days on yellowkey MLS ID: A4682903
REDUCED by $100,000 (4.1%) on 06/03/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1940 Built: 1967 Tax: $9,709 (2025)Community: Horizons WestCondo
Taxes:$9,709
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Middle School: Brookside Middle
Remarks: Experience the pinnacle of island living in this 9th-floor, west-facing penthouse offering sweeping, unobstructed Gulf and Crescent Beach views from Point of Rocks to iconic Siesta Beach, where nightly sunsets paint the sky. Perfectly positioned above Siesta Key’s crystal-white sands, this spacious residence features 2 bedrooms and 2 baths with the rare opportunity to expand to a third bedroom and bath, allowing you to customize your coastal retreat. Highlights include a full laundry room, impact-rated windows, tankless water heater, dual A/C systems, and a coveted private 2-car garage with direct lobby access—one of only four in the community. Located in the prestigious Horizons West, a gated gulf-to-bay enclave spanning more than seven lush acres, residents enjoy 300 feet of private beachfront, beach cabanas, a Gulf-front pool and spa, grilling areas, a bayside pool and clubhouse, and a private intracoastal park with day dock, kayak launch, and serene mangrove setting. With SIRS and Milestone inspections complete and new landscaping throughout, this exceptional penthouse delivers luxury, privacy, and the ultimate Siesta Key beachfront lifestyle.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Suki Scollo (941-587-2289)
6140 MIDNIGHT PASS RD #603, SARASOTA, FL 34242
$1,199,00071 Days on yellowkey MLS ID: A4688546
REDUCED by $26,000 (2.1%) on 05/24/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1521 Built: 1967 Tax: $11,779 (2025)Community: Horizons WestCondo
Taxes:$11,779
Remarks: Perched on the 6th floor with sweeping, unobstructed western views of the Gulf and world famous Crescent Beach, this spectacular Siesta Key condo delivers front row sunsets and frequent dolphin sightings, stretching from Point of Rocks to north Siesta Key. Ideally positioned above the gulf front pool and spa, this partially furnished island retreat is move in ready and features a full length enclosed balcony for added living space, along with impact windows and doors for peace of mind. Located in Horizons West, a coveted gulf to bay resort community spanning over 7 lushly landscaped acres, residents enjoy 300 feet of deeded private beach with cabanas, a beachside pool and spa, grilling areas, a second pool by the clubhouse, and a private Intracoastal Waterway park with day dock perfect for kayaking, paddleboarding, fishing, or relaxing among the mangroves. Conveniently access Siesta Key Village dining, shopping, and entertainment via the free island trolley and embrace the ultimate carefree coastal lifestyle. Come see what Island Life is all about.
3365 RAMBLEWOOD DR N #35C8, SARASOTA, FL 34237
$147,000190 Days on yellowkey MLS ID: A4673749
REDUCED by $11,000 (7.0%) on 03/31/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1104 Built: 1974 Tax: $2,772 (2025)Community: Ramblewood AcresCondo
Taxes:$2,772
Elementary School: Tuttle Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Virtually Staged. Step into Florida living in Ramblewood Acres, a gated community known for its convenience and charm. This impeccably kept, move-in-ready townhome offers a smart, functional layout. Granite counters, brand new stainless steel dishwasher, and a passthrough to the dining area - perfect for everyday living and easy entertaining. The great room and main-level half bath add comfort and practicality. Upstairs, two large bedrooms each feature private en-suite baths and large closets. One offers a serene balcony, the other a generous sundeck, your choice of personal retreat. Fresh new interior paint for the next homeowner and brand new roof to be completed January 2026! Ramblewood Acres offers three pools (including one heated), a dog park, clubhouse, fitness center, tennis courts, playground, and shuffleboard. Fees include basic cable, on-site management, and more for true low-maintenance living. The location puts you close to everything. Downtown Sarasota, St. Armands Circle, and world-class beaches are minutes away. UTC’s shopping and dining are within a short drive, and SRQ Airport is conveniently nearby. Golfers will love having the newly renovated Bobby Jones Golf Course just around the corner. Don’t miss this opportunity—schedule your showing and discover your new home!
Listing is courtesy of: KW COASTAL LIVING II (941-556-0500)
Listing Agent: Lori Sabattini (941-266-1597)
4631 SUMMERWIND DR #16, SARASOTA, FL 34234
$149,90023 Days on yellowkey MLS ID: A4694419
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 966 Built: 1983Monthly Fee: $575 Tax: $2,257 (2025)Community: Summer WindCondo
Taxes:$2,257
Remarks: The best value in Summer Wind is here and it won't last long. This 2 bedroom 2 bathroom condo is move-in ready and perfectly situated on the quiet West end of the community with immediate access to a private park. Summer Wind is conveniently located just 5 minutes from the SRQ Airport and 10 minutes from downtown Sarasota and area amenities. Recent HOA improvements, include new roof (2023), exterior paint and trim (2018), upgraded Pool Area, landscaped entrance, and resurfaced driveway. HOA fees include Community Pool, Exterior Maintenance, Grounds Maintenance, Pest Control, Water, Sewer, and Trash.
Listing is courtesy of: UPTOP REAL ESTATE SERVICES, LLC (941-554-4896)
Listing Agent: Adam Kabinoff (941-554-4896)
1260 DOLPHIN BAY WAY #403, SARASOTA, FL 34242
$1,299,900130 Days on yellowkey MLS ID: A4680107
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1915 Built: 1997 Tax: $7,394 (2025)Community: Dolphin BaySpa: YesCondo
Taxes:$7,394
Remarks: Experience coastal luxury in this beautifully updated 2BR/2BA condo in the gated, waterfront community of Dolphin Bay on Siesta Key. This exceptional 4th floor residence blends modern sophistication with breathtaking Intracoastal Waterway views, creating a serene yet elevated island lifestyle. A charming front porch welcomes you—perfect for relaxing with a favorite beverage while grilling and enjoying city views. Inside, the spacious open-concept floor plan is thoughtfully designed for both comfort and style. Extensive kitchen and bath renovations completed in 2020 showcase contemporary finishes and high-end fixtures throughout. The chef’s kitchen features shaker-style cabinetry, quartz countertops, reverse osmosis system, and a built-in desk area with additional storage—both functional and elegant. The adjoining den, filled with natural light from sliding glass doors, offers a peaceful spot to read or work while taking in tranquil outdoor views. Immaculate hardwood floors flow through the living areas, adding warmth and timeless appeal. The dining room is enhanced by a custom built-in dry bar, ideal for entertaining. Expansive windows and sliding glass doors frame stunning southern views of the Intracoastal Waterway, where boats pass by, dolphins play, and coastal breezes set the mood. The enclosed, tiled lanai extends the living space and provides a perfect setting for gathering with friends and family while enjoying the scenery. The primary suite is a private retreat with its own lanai access, a spacious walk-in closet, and a luxurious en-suite bath featuring a soaking tub and tiled walk-in shower. The guest bedroom offers a private entrance to the front patio, generous storage with two closets (including a walk-in), and direct access to the guest bathroom. Additional features include an interior utility room with cabinetry, a newer hot water heater (2024), newer HVAC system (2018), and washer and dryer (2019)—making this a truly move-in-ready home. Private under-building garage parking and additional storage provide convenience and peace of mind. Dolphin Bay is a pet-friendly community offering resort-style amenities, including a pool & spa, fitness center, clubhouse, three Har-Tru tennis courts, fishing pier, and scenic walking paths. Enjoy an easy stroll or trolley ride to world-famous Siesta Key Beach, renowned for its powdery white sand, Pickleball courts, and laid-back island vibe. Schedule your private showing today and discover the best of Siesta Key living—no hurricane damage from any storms.
Listing is courtesy of: ANDREWS & ASSOCIATES REALTY (941-921-5999)
Listing Agent: Stacey Andrews (941-504-1649)
2155 WOOD ST #26A, SARASOTA, FL 34237
$135,0001 Day on yellowkey MLS ID: A4696768
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 918 Built: 1959 Tax: $2,491 (2025)Community: Park LaneSpa: NoCondo
Taxes:$2,491
Remarks: This is the one! Two bedroom, two bathroom, first floor, back corner unit, directly adjacent to Payne Park in highly desirable Downtown Sarasota at the Retro Chic Park Lane community! Split floor plan for privacy means a primary bedroom with ensuite bath & dedicated full bath for guests. Vintage details include custom built ins and original terrazzo floors! Open living area with glass sliders leads to an enclosed lanai overlooking the lushly landscaped courtyard with inground pool. Recent updates include a New Stove, Microwave, Refrigerator, Water Heater, Roof, Sewer Line & Parking Lot! Embrace the best of Sarasota living with the beautiful Payne Park at your doorstep featuring 29 acres of recreation & relaxation complete with walking trails, bike path, skate park, playground, frisbee golf, tennis courts & more! Dedicated parking space in front of unit, separate & secure storage space & two laundry facilities on site. Adjacent to Publix supermarket, & close proximity to Selby Botanical Gardens, amazing restaurants and urban amenities like the Bayfront Park, weekly farmers market & so much more including the boutiques of St. Armand's circle, white sands of Lido Beach & the world renowned Siesta Key! Perfect choice for a snowbird's winter retreat, in town escape, affordable primary residence or investment property!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Evan Roberts (857-919-0894)
5855 MIDNIGHT PASS RD #510, SARASOTA, FL 34242
$689,0001 Day on yellowkey MLS ID: A4696548
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1976Monthly Fee: $750 Tax: $5,794 (2025)Community: Harbor Towers Yacht & Racquet ClubSpa: NoCondo
Taxes:$5,794
Remarks: **Resort Style Living in the Heart of Siesta Key**,**For Those Who Desire The Active Life Style** Experience the best of Siesta Key living at Harbor Towers Yacht & Racquet Club, a premier waterfront community overlooking Little Sarasota Bay. This beautifully maintained turn-key furnished **2-bedroom, 2-bath residence** features a desirable **split floor plan** and is ideally positioned on the **5th floor**, offering tranquil **Intracoastal Waterway views**. Inside, you’ll find thoughtful updates including **new wood-look vinyl plank flooring in both bedrooms**, along with a **new electric range and microwave** in the kitchen. Enjoy the convenience of a **deeded covered carport**, providing protected parking and added value. Harbor Towers is renowned for its resort-style amenities, including **two heated pools**, a clubhouse with outdoor grilling patio, and a **state-of-the-art fitness center** with cardio equipment, free weights, and sauna. Tennis enthusiasts will appreciate the meticulously maintained **Har-Tru courts**, serviced daily for optimal play. The in house Rental Agency is there to help you rent, with a 2 week minimum rental policy. For boating and water lovers, the on-site **marina with 40 slips equipped with water/electric available on first-come, first-served basis**, along with kayak storage and launch, offers direct access to the Intracoastal Waterway. Residents can relax along the scenic waterway, enjoy shaded seating, or unwind in the waterfront gazebo. Additional perks include bicycle storage and **complimentary access to the Siesta Key Open-Air Trolley**, making it easy to explore the island. You’re just moments from **world-famous Siesta Key Beach**, known for its powdery quartz sand and breathtaking sunsets, as well as Siesta Key Village with its vibrant dining, shopping, and entertainment. The community has recently undergone significant upgrades, including **new stucco exterior, impact-resistant windows, and sliding glass doors**, offering enhanced beauty and peace of mind.
Listing Agent: Julie Kell (330-309-7022)
5813 MERION WAY #5813, SARASOTA, FL 34243
$369,9001 Day on yellowkey MLS ID: S5151519
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1984 Built: 1988Monthly Fee: $450 Tax: $3,337 (2025)Community: Fairway SixCondo
Taxes:$3,337
Remarks: Welcome to Fairway Six at Palm Aire, where picturesque golf course living, beautiful water views, and an exceptional Florida lifestyle come together. This beautifully remodeled and fully furnished 2-bedroom, 2-bathroom home with a versatile flex space/den offers the perfect blend of comfort, style, and convenience. Filled with natural light, the open-concept floor plan features vaulted ceilings, an updated kitchen with granite countertops, and spacious living and dining areas designed for both everyday living and entertaining. The flexible den provides the perfect space for a home office, guest room, or hobby area. The oversized primary suite and thoughtfully designed layout create a welcoming retreat, while the enclosed sunroom and outdoor patio showcase stunning water views, offering the perfect setting to enjoy your morning coffee or unwind at the end of the day. Additional features include an oversized two-car garage, inside utility room, and a prime location directly across from the community pool and tennis courts. Located within the highly desirable Palm Aire community, residents enjoy beautifully maintained grounds, golf course surroundings, walking paths, tennis courts, community pools, and a relaxed Florida lifestyle. Conveniently located near shopping, dining, entertainment, world-class beaches, and major roadways, this home offers the ideal combination of tranquility and accessibility. Whether you're seeking a full-time residence, seasonal retreat, or turnkey Florida getaway, this exceptional waterfront home is ready for you to enjoy. ALL INFORMATION IS INTENDED TO BE ACCURATE IT IS THE BUER AND BUYERS AGENTS RESPONSIBILITY TO VERIFY ALL DETAILS AND INFORMATION
Listing is courtesy of: FLORIDA IN MOTION REALTY INC (407-947-2757)
Listing Agent: Eugene Petriella (321-299-8766)
4805 RILMA AVE #106, SARASOTA, FL 34234
$119,0001 Day on yellowkey MLS ID: A4696327
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 837 Built: 1974 Tax: $1,983 (2025)Community: Summer LakesCondo
Taxes:$1,983
Remarks: Discover this fully updated 2-bedroom, 1-bath condo in the quiet Summer Lakes community of Sarasota. Ideally located just 1 mile from Ringling College and Sarasota-Bradenton Airport, and under 2 miles from USF Sarasota, it offers a 10-minute drive to vibrant downtown Sarasota and 15 minutes to Lido Key and St. Armands Circle. The bright, move-in-ready home features granite countertops, stainless steel appliances, wood cabinets, plantation shutters, and no carpet, plus it comes partially furnished. Enjoy the community pool and assigned parking. Priced as one of the most affordable condos in Sarasota, this gem is perfect for owner-occupants or investors seeking quick possession in a prime location.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-556-2150)
Listing Agent: Miao Whiteside (941-263-9898)
5551 BENTGRASS DR #11-117, SARASOTA, FL 34235
$305,0006 Days on yellowkey MLS ID: A4696165
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1395 Built: 2002Monthly Fee: $656 Tax: $3,109 (2025)Community: Las Palmas Of SarasotaSpa: NoCondo
Taxes:$3,109
Elementary School: Emma E. Booker Elementary
Remarks: Virtually Staged. Welcome to Las Palmas, a gated community where convenience meets resort-style living in one of Sarasota’s most desirable locations. Ideally situated just moments from Benderson Park, UTC Mall, I-75, and dining, with a short drive to world-famous Gulf beaches, downtown Sarasota, hospitals, and the airport. This beautifully updated second-floor end unit offers 3 bedrooms, 2 bathrooms, and an attached one-car garage. Additional windows fill the home with natural light, creating a bright and airy atmosphere. A private entrance and staircase lead to an inviting open-concept layout featuring a desirable split-bedroom floor plan, newly installed flooring, fresh interior paint, updated lighting, upgraded kitchen cabinetry, and elegant quartz countertops in both the kitchen and bathrooms. The screened lanai overlooks a tranquil nature preserve, providing exceptional privacy and peaceful views. A full-size laundry room and generous closet space add everyday convenience. Major updates include a new roof (2024), A/C (2020), and water heater (2022). Residents enjoy an impressive array of resort-style amenities, including two swimming pools, a hot tub, a fitness center, a clubhouse, tennis courts, a playground, a dog park, an outdoor grilling area, a car wash station, and more. Affordable on-site RV and boat storage is also available. Whether you're a first-time homebuyer, investor, or seasonal resident, this exceptional property offers the perfect blend of comfort, style, and location.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Keiko Donnelly (941-544-4664)
5552 BENTGRASS DR #7-116, SARASOTA, FL 34235
$250,0001 Day on yellowkey MLS ID: A4695756
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1615 Built: 2002 Tax: $2,892 (2025)Community: Las Palmas Of SarasotaCondo
Taxes:$2,892
Remarks: GORGEOUS AND PRICED TO SELL! Impressive upgrades, stylish, and great location! Step into the largest three-bedroom, two-bath floor plan in Las Palmas, where thoughtful design meets exceptional updates. This unique residence offers peaceful water views, lush mature landscaping, and a layout that truly stands out. From the moment you enter, you'll be captivated by the second story soaring ceilings, enhanced by an impressive catwalk feature that allows natural light to flood the space. The beautifully updated kitchen, modern laminate flooring, and meticulous upkeep make this home move-in ready. Newer AC system, a newer hot water heater, upgrades kitchen floors, and modern updates throughout. Las Palmas is a highly sought-after gated community offering an unparalleled lifestyle. Enjoy direct access to Benderson Park through a private gate, making morning walks, bike rides, or trips to UTC effortless. No need to worry about parking for special events ... simply stroll or cycle to Sarasota's premier shopping and dining destination. Residents also have access to resort-style amenities, including two heated swimming pools, tennis courts, two clubhouses with a TV room, two fitness centers , a car wash station, a dog park, and even extra storage for RVs and large trucks. This home is a rare find and beautifully maintained, thoughtfully updated, and priced to sell. Don't miss your chance to own one of the best values in Sarasota. This condo is not only exciting to view but it's also priced below well below it's value, and incredibly well taken care of by it's current owners. Schedule your showing today!
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Dawn Bear (941-468-7224)
7461 W COUNTRY CLUB DR N #402, SARASOTA, FL 34243
$165,0003 Days on yellowkey MLS ID: A4694358
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1090 Built: 1973 Tax: $710 (2025)Community: No 1 Palm-Aire Desoto Lakes Cc Apt CondoCondo
Taxes:$710
Remarks: Gorgeous Palm Aire unit with beautiful full view of golf course from the top floor. Updated windows and AC. This condominium is perfect for full time or seasonal living. Or can be used as a rental. Both bedrooms have their own bathroom. Screen balcony to enjoy the breezes and views. Watch the sunrise from the balcony. Close to the university Town Center, restaurants, shopping, supporting services, I-75 and the Sarasota Airport.
Listing is courtesy of: SABAL REAL ESTATE (941-870-0106)
Listing Agent: Carolyn Davis (941-356-5624)
9397 MIDNIGHT PASS RD #905, SARASOTA, FL 34242
$729,000237 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
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)
435 S GULFSTREAM AVE #403, SARASOTA, FL 34236
$625,000247 Days on yellowkey MLS ID: A4667640
REDUCED by $24,500 (3.8%) on 06/11/2026
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
Elementary School: Southside Elementary
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Wake up to Sarasota Bay. Walk to everything else. This is the one you've been waiting for — a fully renovated 2-bedroom, 2-bath residence at The Regency House, where downtown Sarasota's most coveted address meets the shimmering waters of Sarasota Bay. Unit #403 has been thoughtfully reimagined from the inside out, featuring a stunning new kitchen, beautifully appointed bathrooms, and fresh flooring throughout — move-in ready and magazine-worthy. The Regency House is having its moment. A brand-new community pool has been approved, and the seller is covering the assessment in full — so you inherit all the upside with none of the hassle. Step outside and you're already living your best life. Bayfront Park, the vibrant energy of Main Street, world-class dining, arts, and the Saturday Farmers Market — all of it is right here, on foot. This isn't just a home. It's a front-row seat to everything that makes Sarasota one of the most sought-after cities in Florida. For the buyer who refuses to compromise — on location, on lifestyle, or on quality — 435 S Gulfstream Ave #403 is the answer. Schedule your private showing today. Opportunities like this don't wait.
Listing is courtesy of: MEDWAY REALTY (941-375-2456)
Listing Agent: Kim Donahue (941-724-2587)
5711 BENTGRASS DR #19-203, SARASOTA, FL 34235
$239,000378 Days on yellowkey MLS ID: A4654485
REDUCED by $9,000 (3.6%) on 05/19/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1246 Built: 2002 Tax: $3,197 (2024)Community: Las Palmas Of SarasotaSpa: YesCondo
Taxes:$3,197
Remarks: Lease to Own available! Two-bedroom two bath townhome in the popular gated community of Las Palmas. The luxury condominium community of Las Palmas has a superior Sarasota location in close proximity to UTC Mall, Benderson Park, popular local golf courses, downtown activities and local beaches! This gated, resort community offers not one but two heated pools, two gyms, a clubhouse, pickleball, tennis, walking trails, dog park, and playgrounds. The two-bedroom townhouse has a beautiful preserve view from the large, screened lanai. There is a one car garage on first level, large enough to store all your toys and car. The second level has the open kitchen, living room and dining room and a guest bedroom and bath. The 3rd floor has the primary suite with the large bath and walk in closet. The kitchen boasts wood cabinets, quartz countertops and new stainless appliances. This community offers an affordable Florida lifestyle for both the first-time buyer or retiree. Large pets are welcome! Why rent when you can own this home for less, call and ask about the affordable terms.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER (941-729-7400)
Listing Agent: Kathy Cahill (941-807-3565)
1100 IMPERIAL DR #108, SARASOTA, FL 34236
$569,00029 Days on yellowkey MLS ID: A4692243
REDUCED by $30,000 (5.0%) on 06/10/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1262 Built: 1971 Tax: $7,769 (2025)Community: Bays Bluff Atps Sec 1Spa: YesCondo
Taxes:$7,769
Elementary School: Gocio Elementary
Remarks: MOTIVATED SELLER! DON'T MISS THIS OPPORTUNITY! This 1st floor end-unit directly faces Sarasota Bay and offers the ability to walk right out to the bayfront. As the largest floor plan available in Bay’s Bluff, the residence spans the entire width of the building and, with its expansive windows, offers either sunrise or sunset views from every room - - - and wonderful cross breezes! * * * Nicely updated, this unit is move-in ready with some furniture included. Hurricane-impact windows provide added peace of mind. The screened lanai is a wonderful place to sit, relax and watch the seabirds, sailboats, and breathtaking sunsets. * * * Bay’s Bluff is a charming, pet-friendly mid-rise community. Are you a dog lover? Imagine being able to take your dog out directly from your unit and walk with them along the bayfront. * * * The waterfront heated pool and grill area are ideal for hosting a sunset cocktail party or cookout. Or relax at the water’s edge in an Adirondack chair on the community’s 267-foot private seawall, where the soothing sounds of the bay will calm your mind and spirit. * * * Location, location, location! Publix grocery is conveniently located just across the street; The Bay Park, Sarasota’s 53-acre cultural and waterfront destination, is only two blocks away; downtown Main Street is just one mile away, offering easy access to world-class dining, theaters, galleries and shopping; the Sarasota-Bradenton Airport is 4 miles away; and one of Sarasota’s many wonderful beaches lies just on the other side of the Ringling Bridge that you can see from the lanai. * * * Don’t miss this rare opportunity to own a premier bayfront residence in downtown Sarasota, with water views and a prime location.
Listing Agent: Marilyn Kneafsey (941-373-0999)
5855 MIDNIGHT PASS RD #420, SARASOTA, FL 34242
$745,000213 Days on yellowkey MLS ID: A4671788
REDUCED by $20,000 (2.6%) on 06/11/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1976 Tax: $4,975 (2024)Community: Harbor Towers Y & RCondo
Taxes:$4,975
Remarks: Location, location & views! Enjoy and experience luxury living at the Harbor Towers located just steps away from the world-famous Siesta Key beach. Highly desirable 4th floor unit, 2BR/2BTH with spectacular Gulf of America views from every room. Fully updated unit with new windows, new pipes, quartz countertops, new kitchen cabinets doors, new bathrooms and luxury vinyl flooring throughout. This turnkey furnished condo features an open floor plan, two suites split plan bedrooms and provides one parking space & additional storage room. New electrical panel and new water heater. Delight yourself at the HT amenities including heated resort style pools, 3 Har-Tru tennis courts, fitness center, sauna, clubhouse and a superb Marina & seating along the intercoastal waterway. HT has newly renovated building facade, common area including the lobby, spa area and hallways. A fantastic investment opportunity to own a rental income while enjoying the unit whenever you wish. Two-week minimum rentals are allowed 26 times/ year. Buyer can use the on-site property management company for rentals, or others.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Mihaela Dragan (630-330-8903)
1750 BENJAMIN FRANKLIN DR #5F, SARASOTA, FL 34236
$850,00010 Days on yellowkey MLS ID: A4693130
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1781 Built: 1970 Tax: $8,633 (2025)Community: Key Tower SouthCondo
Taxes:$8,633
Remarks: Experience the best of beachfront living at Key Tower South on Lido Beach. The expansive beach views are nothing short of spectacular from the moment you enter the lobby. As your guests enter this spacious 1,781-square-foot residence, their first impression will be the lovely hospitality bar in the large foyer area. This well-appointed unit features a large open living and dining area bordered by a 23 foot long sunroom. * * * There are two generous bedrooms plus a versatile den with a built-in Murphy bed concealed within attractive custom wood cabinetry. Large travertine stone tile flooring flows throughout the main living areas, while the primary suite offers brand-new carpeting, two large walk-in closets, a dual sink vanity, a comfort-height toilet, a walk-in shower and its own private sunroom. Abundant storage throughout the entire residence adds to its everyday convenience and the recessed lighting creates a contemporary feel. The kitchen is well laid out with lots of counter space and areas for admirers or critics to pull up a bar stool and watch the chef work their magic. * * * Enjoy the peaceful eastern exposure on the private terraces off both the living room and primary bedroom, providing inviting sunlit spaces to relax and take in views of the Sarasota skyline, which sparkles beautifully after sunset. One of the home's two air-conditioning systems is brand new and the other was installed in 2022. * * * Key Tower South has undergone extensive renovations, including a complete transformation of the lobby and common areas in 2025. The building also features its own perimeter hurricane and storm-surge protection system for added peace of mind. Residents enjoy 220 feet of private Gulf-front beach, direct beach access, a heated beachfront pool, expansive sun deck, fitness center, saunas, library, bike storage, and on-site management. This exceptional residence offers the comfort, convenience, and lifestyle that make Lido Beach one of Sarasota's most desirable waterfront destinations.
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