Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
5830 MIDNIGHT PASS RD #52, SARASOTA, FL 34242
$595,000230 Days on yellowkey MLS ID: A4664667
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 728 Built: 1963Monthly Fee: $1,231 Tax: $6,077 (2024)Community: Jamaica RoyaleCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,077
Elementary School: Phillippi Shores Elementary
High School: Riverview High
Tax Year: 2024
Middle School: Brookside Middle
Remarks: An investor’s dream! Discover unbeatable income potential with this fully renovated 1 bed, 1 bath condo at Jamaica Royale—a proven high-performing rental generating up to $58,000 annually and already secured with over $30,000 in bookings for 2026. Whether you're seeking a profitable income property, a personal beach retreat, or both, this turnkey unit is positioned to deliver. The spacious open-concept layout features a beautifully upgraded kitchen with peninsula seating, quartz countertops, coordinated backsplash, sleek silver fixtures, and brand-new appliances. Luxury vinyl plank flooring and crown molding create a bright, cohesive coastal aesthetic throughout. The large bedroom includes a king-size bed and generous closet—ideal for extended stays and maximizing guest comfort. The stylish bathroom includes a walk-in shower with coastal tile, glass enclosure, custom vanity, and modern finishes. Perfectly situated just steps from one of Jamaica Royale’s three resort-style pools and a short stroll to Siesta Key’s iconic powder-soft sand, this condo offers the lifestyle renters desire and investors value. With its strong rental history, future bookings in place, and reputation as a top income producer, this property is truly the best of both worlds: a relaxing beach escape and a smart income-generating asset.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Noelle Vihrachoff (570-262-4594)
7374 ROYAL BIRKDALE DR #15D, SARASOTA, FL 34238
$424,0009 Days on yellowkey MLS ID: A4690483
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2282 Built: 1981 Tax: $4,462 (2025)Community: BallantraeVilla
Taxes:$4,462
Elementary School: Gulf Gate Elementary
Tax Year: 2025
Remarks: Welcome to a refined and effortless way of living within the gated, maintenance-free community of Ballantrae ideally positioned near the Palmer Ranch area. Set among 36 acres of lush, park-like grounds, this impeccably maintained end-unit villa offers the privacy of a single-family residence paired with the ease of low-maintenance ownership. Spanning 2,282 square feet of air-conditioned living space, this true three-bedroom, two-bath home features a thoughtfully designed open layout with a renovated kitchen, light cabinetry, and casual dining area flowing seamlessly into expansive living and family rooms, all finished with hard-surface flooring throughout. Natural light fills the interiors, drawing attention to tranquil green views, while an enclosed, vented lanai extends the living space year-round and is enhanced by motorized hurricane shutters. The primary suite serves as a peaceful retreat with a flexible sitting area or office nook, generous closet space, and serene surroundings, while two additional guest bedrooms offer versatility for visitors or workspace. Designed for both comfort and peace of mind, the home includes a brand-new roof (2024), newer HVAC system, updated water heater, replumbing, and full hurricane protection with roll-down shutters on all windows. Ballantrae is known for its quiet, beautifully maintained setting where mature landscaping and open green space create a sense of calm, and its maintenance structure allows for a true lock-and-leave lifestyle. Perfectly located, the home is just minutes from the world-renowned white sands of Siesta Key Beach, the shops and dining of Gulf Gate, and convenient access to Interstate 75 and U.S. Route 41. Downtown Sarasota’s waterfront, restaurants, theaters, and cultural venues are close by, along with leading medical facilities including Sarasota Memorial Hospital and Doctors Hospital of Sarasota, while St. Armands Circle, Lido Key, and Longboat Key are just beyond. Combining thoughtful updates, storm-ready features, and a peaceful natural setting with exceptional proximity to Sarasota’s best offerings, this residence presents a compelling opportunity for full-time living or a seasonal retreat.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Sharon Chiodi (941-809-0380)
711 S PALM AVE #302, SARASOTA, FL 34236
$1,525,00020 Days on yellowkey MLS ID: A4688989
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1815 Built: 2019 Tax: $15,916 (2025)Community: 7 One One PalmSpa: NoCondo
Taxes:$15,916
Elementary School: Southside Elementary
High School: Sarasota High
Remarks: One or more photo(s) has been virtually staged. Positioned in the heart of downtown Sarasota, 711 S Palm Avenue offers a rare blend of privacy, scale, and walkability along one of the city’s most desirable streets. Set just moments from the bayfront, marina, and Sarasota’s top dining and cultural destinations, this residence captures the essence of effortless downtown living. The home is thoughtfully designed with a layout that balances everyday comfort and entertaining, featuring light-filled living spaces, well-proportioned rooms, and a seamless connection between indoor and outdoor areas. Expansive windows invite natural light throughout, while carefully considered design elements create a sense of warmth and livability. The kitchen serves as the central gathering space, designed for both function and hosting, with ample storage, quality appliances, and an easy flow into the main living and dining areas. Private bedroom suites provide comfortable retreats, while the primary suite offers a quiet escape with generous proportions and a well-appointed bath. Outdoor spaces are equally inviting, offering room to relax or entertain while enjoying the energy of downtown just beyond. Whether as a full-time residence or seasonal retreat, the property presents a compelling opportunity to own in a location where everything Sarasota has to offer is just outside your door.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Susan Pelton (941-321-1007)
3332 THORNWOOD RD #3332, SARASOTA, FL 34231
$288,000111 Days on yellowkey MLS ID: A4675963
REDUCED by $4,500 (1.5%) on 04/25/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1450 Built: 1981 Tax: $3,848 (2025)Community: Crooked Creek Sec 1Condo
Taxes:$3,848
Elementary School: Wilkinson Elementary
Remarks: Private Nature Retreat Minutes from Siesta Key What if your Florida home felt like a private nature retreat—yet was only minutes from the world-famous beaches of Siesta Key? This beautifully updated first-floor 2-bedroom, 2-bath residence in the unique Crooked Creek community offers the perfect blend of peaceful surroundings and Sarasota convenience, with lush tropical landscaping, winding pathways, and direct access to the stunning 72-acre Red Bug Slough Preserve. Offering over 1,450 sq ft of living space, this light-filled condo has been thoughtfully updated since 2021. The spacious 10’ x 26’ Florida room has been enclosed with floor-to-ceiling impact windows and sliding glass doors, creating a bright additional living area that brings the beauty of the outdoors in. Interior features include tile flooring throughout, updated bathrooms, recessed lighting, ceiling fans, hallway laundry with washer and dryer (2021), and NEW A/C (2024), new water heater. The kitchen offers wood cabinetry, solid surface counters, a large roll-out pantry, breakfast bar seating, and updated appliances (2023–2024), including a brand-new refrigerator (Dec 2025). Crooked Creek is a peaceful enclave of just 78 residences, thoughtfully designed to blend with the surrounding natural landscape. Residents enjoy direct access to scenic walking and biking trails, fishing, playgrounds, and picnic areas within the beautiful Red Bug Slough Preserve—making this a true nature lover’s paradise. Community amenities include a lar heated pool, tennis and pickleball court, gazebo, grilling area, renovated kitchen at pool with bathrooms and an outdoor shower. Condo owners also have a storage locker in within a large community shed. Each unit comes with one assigned covered carport and includes ample additional parking for guests. The community is financially strong, with HOA fees reduced from $671 in 2025 to $632 per month in 2026. All of this just minutes from Siesta Key Beach, shopping, dining, and everything Sarasota has to offer.
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Phyllis Coviello (941-408-3265)
3300 S BENEVA RD #224, SARASOTA, FL 34232
$215,000471 Days on yellowkey MLS ID: A4634478
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1084 Built: 1980 Tax: $2,437 (2023)Community: Fairways & GreensSpa: NoCondo
Taxes:$2,437
Tax Year: 2023
Remarks: 0.2 mi to Publix • 3 mi to Sarasota Memorial Hospital • 5.5 mi to Siesta Key Beach • Includes Zillow 3D Tour & Matterport Tour Move-in-ready and fully furnished 2-bedroom, 2-bath condominium in a secured elevator building close to Sarasota’s key amenities. This second-floor residence offers approximately 1,084 sq ft of single-level living with a spacious 9' × 14' screened lanai overlooking the community pool. Recent improvements include hurricane-impact windows and a new roof completed last year, providing peace of mind and energy efficiency. The interior features an updated kitchen and bathrooms, wood-style flooring, and an in-unit laundry room for added convenience. The floor plan includes an open living and dining area with direct access to the pool-facing lanai, creating an ideal indoor-outdoor extension of the living space. The primary suite offers ample storage and an updated bath, while the guest bedroom and additional full bath provide flexibility for visitors or home workspace needs. This condo also includes one assigned covered parking space plus abundant guest parking throughout the community. From this central Sarasota location, reach Arlington Park (2.5 mi) for aquatic facilities, fitness center, tennis, pickleball, basketball, and walking paths. Explore Downtown Sarasota (4 mi) for dining, shops, and Bayfront Park, or head to Siesta Key Beach (5.5 mi) for world-famous coastline. Additional anchors include Legacy Trail access (2.2 mi), Walmart Neighborhood Market (0.9 mi), Starbucks (1.2 mi), Westfield Siesta Key (2.5 mi), and direct routes via US-41 (2 mi) and I-75 (3.8 mi). This furnished condominium combines an updated interior, secured lobby access, an elevator, pool views, and proximity to Sarasota’s beaches, parks, shopping, and medical services. Be sure to view the Zillow 3D Tour and Matterport walk-through for a complete look at the layout and features of Unit 224.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Jill French (941-600-8281)
161 VISTA HERMOSA CIR #26-A, SARASOTA, FL 34242
$539,000202 Days on yellowkey MLS ID: A4667260
REDUCED by $20,000 (3.6%) on 04/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1265 Built: 1971 Tax: $4,555 (2025)Community: Vista HermosaVilla
Taxes:$4,555
Remarks: Price Reduction! One of the best Values on Siesta Key! Discover the perfect blend of privacy, convenience, and income potential with this beautifully renovated, freestanding Villa located in the heart of Siesta Key. Tucked away in the sought-after Vista Hermosa community, this light-filled retreat offers the feel of a private home with all the benefits of low-maintenance island living. This newly renovated, two bedroom two bath, Villa showcases: impact windows and doors, stainless steel appliances, ceramic plank flooring throughout, Washer/Dryer and beautiful, coastal furnishings. Just a short stroll brings you to the powdery sands of Crescent Beach, one of the Gulf Coast’s most beloved spots for sun, surf, and stunning sunsets. Whether you're looking for a personal coastal getaway or a lucrative investment, this villa delivers – with biweekly rental options that allow you to generate steady income throughout the year. Inside, enjoy a freshly updated interior featuring modern finishes and a bright, open layout. Outside, hop on the free Siesta Islander Trolley for easy access to vibrant Siesta Village, where you'll find charming shops, restaurants, and entertainment. This is your chance to own a move-in ready, income-producing villa in one of Florida’s most desirable beach communities. Home is being offered turn key furnished.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Joe Kesslak (941-321-8585)
901 BEACH RD #205, SARASOTA, FL 34242
$639,00045 Days on yellowkey MLS ID: A4686468
REDUCED by $10,000 (1.5%) on 04/21/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 753 Built: 1972 Tax: $5,156 (2025)Community: La Siesta CondominiumsCondo
Taxes:$5,156
Remarks: Welcome to the iconic La Siesta Condominiums, directly across from the main beach access of Siesta Key where coastal charm meets effortless beach days. Perfectly positioned just 100 steps from the powdery sands of Siesta Key Beach, this beautifully appointed turnkey furnished second floor condo offers breathtaking Gulf views and an unmatched connection to one of the nation’s most iconic shorelines. Designed for prime vacationing, this income producing vacation rental features an updated interior with coastal-inspired finishes including a modern kitchen, luxury vinyl plank flooring and a dining area. The primary bedroom has a king bed, secondary bedroom features two twin beds, and a queen sleeper sofa in the living room. The open-concept living space is filled with that special Siesta Key sunshine that just hits differently. You are met with a seamless flow between indoors and out featuring a hurricane rated slider door that leads you to a private balcony that becomes your front-row seat to unforgettable sunsets over the Gulf of Mexico. Ideal for both personal enjoyment and income potential, this investor-friendly property allows for up to 52 weeks of rentals annually, offering exceptional flexibility and the opportunity to maximize returns in one of Florida’s most sought-after beach destinations utilizing the professional full-time rental management program. At La Siesta, you’ll enjoy resort-style amenities including a heated pool, fitness center, clubhouse, grilling stations, on-site laundry, a covered parking space and additional storage are also included. With a seven-day rental minimum and strong demand year-round, this unit offers excellent income potential, with bookings already secured into 2026. Located just minutes from the vibrant charm of Siesta Key Village and the south bridge, you’ll have easy access taking the Siesta Key trolley to boutique shopping, waterfront dining, and experience the laid-back island nightlife. Let’s make this coastal paradise a part of your story!
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Ann Allen (407-949-4457)
2424 ASHTON RD, SARASOTA, FL 34231
$2,642,5006 Days on yellowkey MLS ID: A4691268
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2872 Built: 2026 Tax: $5,146 (2025)Community: Phillippi CrestSpa: YesSingle Family
Taxes:$5,146
Remarks: Pre-Construction. To be built. Pre-Construction To Be Built, 1-Acre Homesite, no flood zone, Subdivision Potential, Fully Customizable Dream Home Bring your dream home to life with this upcoming custom-built estate by E/M Custom Homes, perfectly situated on a spacious 1-acre, non-deed-restricted homesite, offering the freedom to live your way with no HOA rules or limitations. Even more, the lot has already been approved to be subdivided into four separate parcels, presenting a rare opportunity for future investment, expansion, or multi-generational living. Thoughtfully designed for both luxury and everyday comfort, this home features an expansive open-concept layout anchored by a stunning great room with elegant coffered ceiling beams. The gourmet kitchen serves as the heart of the home, complete with a large center island, sleek quartz countertops, and premium wood cabinetry, ideal for entertaining and daily living alike. The flexible floor plan includes three bedrooms, a dedicated den, and a versatile bonus room, allowing you to tailor the space to fit your lifestyle, whether you envision a home office, fitness studio, or media room. A spacious three-car garage provides ample room for vehicles, storage, or recreational equipment. Enjoy Florida living at its finest with a covered lanai and summer kitchen, perfect for creating your own outdoor oasis. With no deed restrictions, there is plenty of room to expand, store boats or RVs, or design your ideal backyard retreat. Ideally located just 2.5 miles from Siesta Key, minutes to Downtown Sarasota, and offering easy access to Interstate 75, this property combines privacy with convenience. It is also situated within a top-rated school district featuring excellent magnet schools. E/M Custom Homes is known for quality craftsmanship and personalized design-build services, and there is still time for buyers to select finishes and customize the home to their exact vision. Photos are of a recently completed model and are for illustrative purposes only.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Pat Rodriguez (941-685-5805)
847 FREELING DR, SARASOTA, FL 34242
$3,950,0006 Days on yellowkey MLS ID: A4690268
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4034 Built: 1954 Tax: $40,498 (2025)Community: Bay Island ShoresSpa: YesSingle Family
Taxes:$40,498
Remarks: Located in the highly sought-after Bay Isles community on Siesta Key, this property at 847 Freeling Drive offers a rare opportunity to customize and create your ideal coastal home. Positioned on the first street onto Siesta Key, the location provides exceptional convenience to the bridge, mainland, and all that the island has to offer. The home features 4 bedrooms and 4.5 bathrooms, with the upper level remaining intact and in great condition. The ground level experienced flooding during the recent hurricanes; however, the seller has already completed professional remediation, providing a clean slate for updates and renovations to suit your vision. Situated on a protected deep-water basin, the property is ideal for boating and waterfront living, complete with a private dock, no fixed bridges, and direct access just minutes to the Gulf. The home also features a pool, offering the perfect foundation to create a true coastal retreat. This is a unique opportunity to secure a well-located waterfront property and finish it to your exact specifications in one of Siesta Key’s most desirable communities.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Michelle Ward (941-920-2460)
2632 SUNNYSIDE ST, SARASOTA, FL 34239
$395,0007 Days on yellowkey MLS ID: A4690325
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1578 Built: 1957Monthly Fee: $17 Tax: $4,699 (2025)Community: South GateSingle Family
Taxes:$4,699
Remarks: Charming mid-century modern 3 bedroom, 2 bathroom home with an oversized 2-car garage, located in the established, deed-restricted South Gate neighborhood of Sarasota. Offering classic Florida style, the home features original terrazzo flooring throughout the home with the exception of ceramic tile in the kitchen and a functional layout with a spacious primary bedroom that includes an en-suite bathroom and walk-in closet. The living room features a built-in bookshelf, and an enclosed sunroom offers flexible space for a home office or additional family area. The home retains original features and offers ample storage throughout, plus a bonus workshop suitable for hobbies or projects. Recent updates include AC replacement (2023) a new garage door (2023), and brand-new toilets. Home is connected to county sewer and comes with Hurricane shutters. The optional South Gate Community Association offers access to a community pool and community center, including the architecturally significant Victor Lundy-designed property with events and weekly classes. Located in the highly sought-after Southside Elementary school district and near Southside Village, Sarasota Memorial Hospital, and just minutes to Siesta Key Beach, with convenient access to shopping, dining, and everyday amenities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Rachel Harvey (941-726-9300)
5924 MIDNIGHT PASS RD #507, SARASOTA, FL 34242
$1,250,0006 Days on yellowkey MLS ID: A4689477
0 Days Off yellowkey (back on 4/24/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1195 Built: 1971 Tax: $12,802 (2025)Community: Sarasota Surf & RacquetSpa: NoCondo
Taxes:$12,802
Remarks: An exceptional opportunity to secure a Gulf-front residence in the highly sought-after Sarasota Surf & Racquet Club on Siesta Key. Positioned on the 5th floor, this two-bedroom, two-bath condominium offers sweeping, unobstructed views of the Gulf of Mexico?the kind of breathtaking backdrop that defines true beachfront living. With 1,195 square feet of interior space plus an expansive 200-square-foot lanai, the layout provides the perfect canvas to create a custom coastal retreat tailored to your personal vision. From sunrise reflections to vivid sunset skies, the panoramic water views take center stage from the main living areas and outdoor space, delivering an ever-changing coastal experience. Sarasota Surf & Racquet Club is known for its prime beachfront location and resort-style setting, offering residents access to a wide array of amenities including tennis courts, swimming pools, fitness facilities, and direct access to Siesta Key?s world-renowned white sand beach. The community?s established reputation and desirable location continue to make it a favorite for both personal enjoyment and long-term investment. Offered at a compelling value reflective of its unique opportunity, this residence presents a rare chance to sec
Listing Agent: Rudy Dudon (941-234-3991)
3174 REGATTA CIR, SARASOTA, FL 34231
$438,9008 Days on yellowkey MLS ID: A4689148
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1279 Built: 1963Monthly Fee: $6 Tax: $4,089 (2025)Community: Gulf GateSpa: NoSingle Family
Taxes:$4,089
Remarks: Bright and light, charming, nicely updated two bedroom, two bath home sold TURNKEY furnished in the lovely Gulf Gate community on a quiet circle street! Don’t miss this tropical oasis with a beautiful backyard and screened in patio ready for new owners – just bring your toothbrush! This community has an optional HOA and no CDD fees! This one car garage home includes the following updates: new exterior paint 2026, new interior paint in 2021, new wind rated sliding doors in 2021, new screened in patio 2021, new range and refrigerator in 2021, new garage exterior door in 2024, garage painted in 2023, new gas grill in 2026, new updated lighting in 2021, and new HVAC installed in 2020. Close to shopping, restaurants, and only 3.9 miles to the famous #1 Beach in the USA - Siesta Key! Enjoy as your personal home or as a great investment opportunity. Don't miss this home, make your appointment to see today!
Listing Agent: Alice Lewis (941-402-5564)
2102 COUNTRY MEADOWS PL, SARASOTA, FL 34235
$475,000301 Days on yellowkey MLS ID: A4657917
REDUCED by $13,900 (2.8%) on 04/07/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1921 Built: 1986Monthly Fee: $46 Tax: $5,003 (2024)Community: Country MeadowsSingle Family
Taxes:$5,003
Elementary School: Gocio Elementary
High School: Booker High
Remarks: Under contract-accepting backup offers. It’s all about the Location! Completely renovated pool home with an Outdoor Oasis. This meticulously remodeled residence is move in ready offering comfort, convenience, and lifestyle. The serene setting offers a peaceful views and privacy. Exterior Highlights Include: New Roof - A new roof ensures peace of mind and long-term durability. Freshly Painted - The beauty of a freshly painted exterior enhances the home’s curb appeal. New Pool Surface - Dive into relaxation with a sparkling pool. Expansive Covered Lanai - Large shaded area for kicking back with your friends and family. Spacious Backyard - Enjoy your fenced for privacy, expansive backyard, perfect for gatherings, play, or quiet time. Interior Features Include: Welcoming Split Floor Plan - Enjoy a warm and inviting layout that offers privacy with guests and spaciousness. Tile Flooring in Main Living Spaces - The primary bedroom, kitchen, dining, and living areas feature stylish and easy-to-maintain pet friendly tile flooring. New Carpet - Experience luxury with natural carpet in the 2 additional bedrooms. Updated Bathrooms - No need to remodel here just move in and enjoy. Modern Kitchen - This modern kitchen make cooking and entertaining a breeze! Warm tones balance with bright light making the room welcoming and inviting. New Appliances – Ready for a Chef. Two-Car Garage - You’ll find plenty of storage in this oversized garage with enough room for two cars, storage and laundry space. Only Minutes from Lakewood Ranch, Medical Centers, Nathan Benderson Park with world class rowing events, premier sports fields and world class beaches. Convenient to Downtown Lakewood Ranch shopping, restaurants, entertainment, and UTC Mall. Easy access to I-75, Sarasota Airport, Tampa International Airport, and Tampa/St. Petersburg.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-360-7777)
Listing Agent: Andrew Barnard (941-920-2001)
116 GARDEN LN, SARASOTA, FL 34242
$1,995,000174 Days on yellowkey MLS ID: A4671064
REDUCED by $155,000 (7.2%) on 04/20/2026
Bed: 4 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2971 Built: 2017 Tax: $20,113 (2024)Community: Siesta Rev OfSingle Family
Taxes:$20,113
Remarks: Effortless Island Living on Siesta Key’s Coveted North End. Discover the perfect blend of modern luxury and low-maintenance living in this contemporary coastal retreat, ideally located on the quiet North End of Siesta Key. Enjoy deeded beach access, mesmerizing Gulf and Big Pass views, and effortless proximity to Siesta Village, the North Bridge, and downtown Sarasota. Built in 2017 to the highest standards by MGB—My Green Building—this four-level residence was designed for comfort, efficiency, and peace of mind. Solid construction, energy-smart design, impact-rated materials, and a brand new A/C system (March 2026) make it the ideal lock-and-leave home for those seeking a worry-free coastal lifestyle. Light-filled living spaces flow seamlessly between the gourmet kitchen, dining, and family areas, all centered on the third floor for optimal views and connection. The private primary suite spans the top level with its own balcony retreat, while three guest bedrooms on the second floor offer space for family or friends. An elevator connects all four floors for easy access, and the flexible lower level provides extra room for a fitness area, studio, or media lounge. Designed for those who value quality, comfort, and ease, this home offers all the benefits of coastal living—without the upkeep. From morning beach walks to sunset cocktails overlooking the Gulf, every day here feels like a vacation.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Gerard Healy (941-961-2240)
1200 E PEPPERTREE LN #307, SARASOTA, FL 34242
$669,00062 Days on yellowkey MLS ID: A4683608
REDUCED by $30,000 (4.3%) on 04/20/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1466 Built: 1973 Tax: $7,547 (2025)Community: Peppertree Bay IiCondo
Taxes:$7,547
Remarks: Set within Peppertree Bay on Siesta Key, 1200 E Peppertree Lane #307 offers a well-proportioned, turnkey, move-in ready two-bedroom, two-bath residence encompassing 1,466 square feet. The interior presents a bright, open layout anchored by a spacious great room, where crown molding, tile flooring throughout, and an expansive wall of impact glass windows create an airy, light-filled living environment. The adjoining dining area flows seamlessly into the kitchen, reinforcing the home’s functional, connected design. The kitchen features a tray ceiling with inner crown molding, recessed lighting, abundant wood cabinetry, granite countertops, a tile backsplash, and a full suite of stainless-steel newer Whirlpool appliances. A breakfast bar provides additional prep and serving space, supporting both everyday living and casual entertaining. The primary bedroom is generously scaled and benefits from strong natural light, crown molding, a walk-in closet, and direct access to the enclosed sunroom. The primary bath includes a granite-topped vanity, glass-enclosed walk-in shower, linen storage, and updated fixtures. A well-sized guest bedroom with an oversized window alcove and a nearby full bath maintains privacy and flexibility for visitors. An enclosed sunroom lined with windows extends the living space, offering versatility as a lounge, office, or secondary sitting area. A stacked washer and dryer are conveniently positioned within a dedicated closet. Newer HVAC system (2024) and Water heater (2025). Peppertree Bay is a Gulf-to-Bay community providing private deeded beach access, a fishing pier, two resort-style heated pools, clubhouses, a fitness center, saunas, tennis and pickleball courts, covered under building assigned parking with this unit that provides a bicycle rack and unit storage, and multiple outdoor gathering areas. This building has newer elevators along with stairwell access, with the building roof being replaced in 2020. The location places residents directly on Siesta Key, home to Siesta Beach, consistently ranked the #1 beach in the United States by TripAdvisor, further underscoring the appeal of both the setting and lifestyle offered by this residence.
5618 ASHTON LAKE DR #5618, SARASOTA, FL 34231
$354,900135 Days on yellowkey MLS ID: A4675431
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1233 Built: 1989Monthly Fee: $325 Tax: $3,158 (2024)Community: Ashton Lakes 03Condo
Taxes:$3,158
Remarks: Virtually staged. Welcome to 5618 Ashton Lake Drive, in Ashton Lake Community. A beautifully remodeled first-floor condo offering a spacious open-concept layout with 2 bedrooms and 2 full bathrooms. Thoughtfully updated throughout, the home features modern finishes in timeless neutral tones, creating a bright and inviting atmosphere. The living and dining areas flow seamlessly into the updated kitchen, perfect for both everyday living and entertaining. New hurricane-rated sliders enhance both safety and energy efficiency while framing stunning lake views and allowing abundant natural light, with the convenience of a private one-car garage and easy first-floor access. Nestled in a quiet, two-story building, this condo offers easy access to Ashton Lakes’ resort-style amenities—33 lush acres, 4 scenic lakes, 2 heated pools (one with a lap lane), tennis & pickleball courts, shuffleboard, and a clubhouse. A pedestrian bridge provides direct access to Detwiler’s Market, CVS, and nearby shopping and dining. Conveniently located near I-75 and Route 41, with easy access to shopping, schools, restaurants, and hospitals. This move-in-ready residence combines comfort, style, and tranquility in a highly desirable setting.
Listing is courtesy of: MEDWAY REALTY (941-375-2456)
Listing Agent: Elena Durez (847-338-6413)
2068 SUNNYSIDE LN, SARASOTA, FL 34239
$895,00028 Days on yellowkey MLS ID: N6143339
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1722 Built: 1953 Tax: $2,984 (2025)Community: Hibiscus Park 1Spa: NoSingle Family
Taxes:$2,984
Remarks: One or more photo(s) has been virtually staged. Get ready to view and call your home in this pristine and immaculate kept move in ready. This stunning Mid-Century Modern residence located in the heart of the highly sought-after Southgate neighborhood! Minutes to Sarasota Hospital and Downtown Sarasota. This beautifully original quality 3-bedroom, 2-bathroom home with one bathroom is a pool bathroom. Original terrazzo flooring, solid wood doors, real wood cabinets and other quality designs with the history craftsmanship still installed of 1953 with updated functionality. As you walk around your home, feel the unique timeless design of a functional kitchen, all appliances included with even a gas stove. Move into your traditional spacious dining area for meals with family and friends. Wonder into the true comfort of an intimate family room, which leads into a spacious filled with natural light Florida room, air condition. Currently as an artist studio with many future possibilities. Open your French doors and seek out to an oversize Pool and lanai and enjoy a beautiful outside sanctuary retreat at the comfort of your home. But it does not end there. Walk out beyond your lanai to your well-kept private landscaping. Total property sits on 0.349-acre lot. Seamlessly blends timeless design with modern luxury and functionality. Step inside again and view your spacious master bedroom with two additional bedrooms. Recent upgrades provide peace of mind and exceptional value, including hurricane-impact windows, new roof installed in 2019. Recently re-plumbed and new water heater. This type of quality home is unmatched. Enjoy the freedom of no HOA fees while being conveniently located all of what Sarasota offers. This home is timeless quality with of style, comfort, and location in one of Sarasota’s most desirable neighborhoods. Schedule your private showing today and experience Southgate living at its finest.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Lenny Lesaltato (941-350-9238)
3165 REGATTA CIR, SARASOTA, FL 34231
$485,00062 Days on yellowkey MLS ID: A4683961
REDUCED by $14,000 (2.8%) on 04/19/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1193 Built: 1964Monthly Fee: $6 Tax: $3,638 (2025)Community: Gulf GateSingle Family
Taxes:$3,638
Remarks: Completely remodeled with all work permitted and completed to the highest standards, this move-in ready Gulf Gate home lives large and showcases exceptional quality, thoughtful design, and true craftsmanship. Live where others vacation — perfectly positioned just 2.4 miles from the nearest Siesta Key beach access, placing world-renowned white sand beaches and breathtaking Gulf sunsets just minutes from your doorstep! The designer-curated kitchen features solid wood white shaker cabinetry, premium quartz countertops, a custom tile backsplash, and new stainless-steel appliances. Just off the kitchen, a spacious dining area is anchored by a beautifully crafted custom solid wood banquette with an integrated bookcase, bench seating, and built-in storage — a rare and functional design feature. Both full bathrooms have been beautifully renovated with new vanities, updated countertops, and custom tiled showers. Additional interior upgrades include new luxury vinyl plank flooring, fresh interior and exterior paint, new doors and trim, and updated lighting & fixtures. Indoor laundry adds everyday convenience. Major system improvements provide peace of mind, including new PVC underground sewer drain lines, new water lines, a new water heater, updated electrical panel, HVAC (2020), and a *BRAND NEW ROOF* (2026)! All windows are equipped with hurricane shutters. Designed for seamless indoor/outdoor living, multiple sliding glass doors open to a spacious screened and covered back porch featuring upgraded Trex decking — the perfect space for morning coffee or relaxed evenings under the twinkle lights. The backyard is truly special, highlighted by a custom PAVER FIRE PIT with built-in bench seating. Enjoy fresh landscaping, a new front paver walkway, and a large fenced backyard. Covered carport parking includes an outdoor storage closet, plus an additional shell parking space which provides plenty of parking. Centrally located on a quiet circle in prime Gulf Gate, this home offers easy access to world-famous Siesta Key Beach and is within walking or biking distance to an array of local restaurants and shopping in Gulf Gate. Publix, Trader Joe’s and Costco are all just minutes away, and Gulf Gate Elementary School is right around the corner. Solid short-term rental history available upon request. Turnkey furnishing option is also available which could make for an easy second home and/or Airbnb. Bright, cheerful, and beautifully finished — this home is truly move-in ready! Buyer’s agent to verify all MLS information including room sizes, utilities and HOA if applicable.
Listing is courtesy of: CARMEL PROPERTIES (941-416-6300)
Listing Agent: Jonah Wright (941-932-1661)
2562 ASHTON RD, SARASOTA, FL 34231
$289,00049 Days on yellowkey MLS ID: A4685871
2 Days Off yellowkey (back on 4/24/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 592 Built: 1930 Tax: $1,359 (2025)Community: Wades SubSingle Family
Taxes:$1,359
Remarks: Under contract-accepting backup offers. Located in one of Sarasota’s historic areas, this one-of- kind, thoughtfully updated cottage blends timeless charm with modern comfort. Beautifully maintained and move-in ready, this 2-bedroom, 1-bath home features a bright, inviting interior, a comfortable layout, and a warm atmosphere that instantly feels like home. The property also includes a charming, covered gazebo surrounded by mature trees and fragrant vines—an ideal setting for relaxing or entertaining guests. With its delightful curb appeal, cheerful living spaces, and stylish cottage character, this home is perfect for buyers seeking something truly special. Recent improvements provide added peace of mind and include a newer roof (approximately 4 years old), updated plumbing and electrical, modern kitchen appliances, and three mini-split HVAC systems installed within the past 3–4 years.Whether you're searching for a primary residence, seasonal getaway, or investment opportunity, this Sarasota gem offers exceptional versatility. Conveniently located near shopping, dining, parks, downtown Sarasota, and the area’s renowned beaches—including Siesta Key—this home perfectly captures the charm, convenience, and easy lifestyle of Florida living.
Listing Agent: Kelly Mooney (941-587-8430)
850 S TAMIAMI TRL #506, SARASOTA, FL 34236
$210,000275 Days on yellowkey MLS ID: A4659953
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 576 Built: 1998 Tax: $3,013 (2024)Community: Central Park Sec 2 Ph 1Spa: YesCondo
Taxes:$3,013
Remarks: One or more photo(s) has been virtually staged. Seller just installed a new washer & dryer, new hot water tank, new bathroom vanity and painted much of the condo. Central Park II is the best-kept secret in Sarasota real estate: Country club amenities, a peaceful environment, relatively low prices--and all across the street from the southern edge of the downtown core. This particular ground-floor condo is a one-bedroom/one-bathroom upgraded unit with stainless-steel appliances, brand new water heater, etc, is situated in one of the best locations within the community: You'd be looking out at the pond, with the pool and court on the other side. Publix is directly across the street and the Legacy Trail is behind it. Downtown and the bayfront are to the north--and Sarasota Memorial Hospital is a few blocks south. Your timing to buy couldn't be better. It's a buyer's market and prices are $75k-$150k lower than a few years ago. Central Park II is also a great place to rent a condo Savvy investors have had no trouble keeping their place leased. It's a stable community with healthy reserves, an active population and lots of clubs and committees if you're so inclined. Easy to show, unit is vacant.
Listing Agent: Ray Collins (941-228-0091)
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