Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
9397 MIDNIGHT PASS RD #905, SARASOTA, FL 34242
$749,000181 Days on yellowkey MLS ID: A4669008
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1348 Built: 1975 Tax: $5,944 (2025)Community: Pointe On Midnight PassCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,944
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: 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)
140 SOUTHWINDS DR, SARASOTA, FL 34231
$217,00054 Days on yellowkey MLS ID: A4683187
3 Days Off yellowkey (back on 4/5/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1475 Built: 2006Monthly Fee: $195 Tax: $1,455 (2025)Community: South Winds Mhp Co-OpManufactured Home
Taxes:$1,455
High School: Riverview High
Remarks: Under contract-accepting backup offers. Welcome to Southwinds, one of Sarasota’s most desirable 55+ active communities! This well-maintained 2006 manufactured home offers the perfect blend of comfort, space, and affordability — ideal for year-round residents or seasonal snowbirds looking for an easy Florida lifestyle. Situated on a private corner lot shaded by mature trees, this home features a spacious open floor plan filled with natural light and comes with: covered carport * private storage shed for tools and extra storage * Dedicated laundry room with washer, dryer, utility sink, and built-in shelving. The bright kitchen offers granite countertops, a center island, and plenty of cabinet space for storage and meal prep. The living room features vaulted ceilings with crown molding and opens to the dining area, creating a comfortable open layout. Two sliding glass doors lead to the deck and bring in great natural light. The primary suite is designed for comfort and relaxation, featuring an en-suite bath with an oversized soaking tub, separate walk-in shower, and ample vanity space. Two guest bedrooms — both with closets — provide flexibility for visitors, hobbies, or a home office. The guest bathroom includes a tub/shower combo. Southwinds is one of only four resident-owned manufactured home parks in Sarasota. The low HOA fee of just $195 a month includes cable and water — a rare value in today’s market. Residents enjoy an active social calendar with hobby clubs, exercise classes, and community gatherings, creating a welcoming and friendly atmosphere. Conveniently located near shopping, dining, medical facilities, and just a short drive to Sarasota’s beautiful Gulf beaches, this home offers affordable living in a vibrant 55+ community. Whether you’re looking for a winter retreat or a full-time Florida residence, this move-in ready home checks all the boxes.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Rachel Harvey (941-726-9300)
116 GARDEN LN, SARASOTA, FL 34242
$2,150,000162 Days on yellowkey MLS ID: A4671064
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
Tax Year: 2024
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)
2414 VACCARO DR, SARASOTA, FL 34231
$983,000100 Days on yellowkey MLS ID: A4677299
REDUCED by $57,000 (5.5%) on 04/04/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2330 Built: 2014Monthly Fee: $570 Tax: $6,350 (2025)Community: Esplanade By Siesta KeySingle Family
Taxes:$6,350
Remarks: NEW PRICE Best Value in the Neighborhood. Live the Florida lifestyle. Located behind the gates of the sought-after Esplanade by Siesta Key, a beautifully appointed 3-bedroom, 3-bath residence with den and extended lanai, showcasing the highly desirable Lazio VII floor plan with tranquil water views. Curb appeal is enhanced by a striking stone façade, an expansive paver driveway, and lush landscaping supported by an automated sprinkler system with reclaimed water—along with ground maintenance, all included in the HOA. Step inside to discover an open-concept design ideal for both entertaining and everyday living, highlighted by new luxury vinyl flooring throughout main living area. The casual yet elegant kitchen is the heart of the home, featuring upgraded cabinetry with hidden hinges, decorative dentil molding, soft-close sliding drawers, granite countertops, a large gathering island, stainless steel appliances, double ovens, and a natural gas cooktop. This home offers three newly updated bathrooms, thoughtfully designed for modern living with high-end finishes and outstanding features. Additional upgrades include Low-E double-pane windows for energy efficiency, hurricane shutters, and Kevlar hurricane panels for the lanai and front door, providing peace of mind and easy storm preparedness. Recent improvements include new exterior waterproof paint, a new A/C system with UV light, a whole-house carbon water filtration system, and a reverse osmosis system under the kitchen sink. Elegant architectural details abound, including tray ceilings, tall interior doors, plantation shutters, and crown molding. The spacious primary suite features an oversized walk-in closet with custom built-in cabinetry.Perfectly situated just minutes from premier shopping, dining, and world-class entertainment—and only a short drive to the powdery sands of Siesta Key Beach—this meticulously maintained home offers luxury, comfort, and location in one remarkable package
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-556-2150)
Listing Agent: Ellen Wilson (704-651-6322)
3941 HAMILTON CLUB CIR #9, SARASOTA, FL 34242
$2,290,00036 Days on yellowkey MLS ID: A4685652
REDUCED by $100,000 (4.2%) on 04/02/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2856 Built: 1989Monthly Fee: $1,400 Tax: $15,416 (2025)Community: Hamilton ClubSingle Family
Taxes:$15,416
Remarks: PRICE IMPROVEMENT... Located in the highly sought-after Hamilton Club community on Siesta Key, this beautifully updated 3-bedroom, 3.5-bath residence offers the ideal blend of coastal comfort, boating convenience, and island living. A large screened-in porch overlooking the water provides a peaceful setting to enjoy morning coffee and gentle coastal breezes. Designed for both everyday living and entertaining, the home features a new private elevator, impact windows and doors, and your own private 10,000-lb boat lift with quick access to the water, making it easy to enjoy boating and the surrounding waterways. Each well-appointed bedroom offers its own private en-suite bathroom, providing exceptional privacy for family and guests. The residence has been thoughtfully upgraded with kitchen updates completed in 2023, updated lighting throughout (2023), fully renovated bathrooms (2022–2023), and new wood flooring, creating a fresh, modern aesthetic with timeless coastal appeal. Additional improvements include a new water softener and water pressure pump installed in 2025, enhancing everyday comfort and functionality. The home is offered furnished or unfurnished, allowing buyers the flexibility to move right in or personalize the space to their style. Hamilton Club residents will also enjoy new community landscaping scheduled for this summer, with exterior building painting planned for 2027, both covered within HOA dues for added peace of mind. Ideally located just minutes from Siesta Key’s world-famous beaches, dining, and shopping, this residence offers an exceptional combination of water views, private boating access, modern upgrades, and relaxed island living.
Listing Agent: Jennifer Thompson, Pa (941-928-0790)
1621 BAY POINT CT, SARASOTA, FL 34236
$5,950,00053 Days on yellowkey MLS ID: A4683737
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3645 Built: 2025 Tax: $18,935 (2025)Community: The Mooring At Bay PointeSingle Family
Taxes:$18,935
Elementary School: Southside Elementary
Remarks: Welcome to a new (built in 2025) and extraordinary single-family waterfront home on the serene and beautiful Hudson Bayou - a premier, tranquil location that feels worlds away while reflecting the vibrancy of the city just moments away. This isn’t just a house, it’s your gateway to the very best of downtown living, and perhaps a viable in-town condominium alternative, with generous guest parking, low-maintenance landscape and NO ASSOCIATION DUES. Nestled in one of the city’s most coveted locations, this beautifully designed residence is just steps from the world-renowned Selby Botanical Gardens- where bayfront beauty, exotic orchids, and lush tropical landscapes await. You are also steps away from the vibrant heart of Downtown Sarasota, the serene Bayfront Park for sunset strolls and events and the city’s central marina. Inside you’ll be captivated by the thoughtful design and an ingenious use of space throughout. The main floor features a large and comfortable open floor plan of great room and kitchen, a luxurious primary suite, an en-suite guest bedroom plus an office. The main living area opens to a lovely private patio with plunge pool and spa overlooking garden and water views. Plus your own private boat dock, featuring a 13,000 lb boat lift and 67 feet of waterfront Upstairs 2 generous en-suite bedrooms await with luxuriously designed baths, each with access to an oversized second story terrace. In addition, this level features a large gym with sauna and a second office. Every inch of this home exudes quality and modern luxury: a show-stopping kitchen with top-tier appliances, a large central island perfect for gathering and entertaining, and a cleverly concealed walk-in pantry behind custom cabinet doors that keeps everything beautifully organized and out of sight. From the high-end finishes, to the seamless indoor-outdoor flow, this detail-filled home combines quality, elegance, and functionality with the unbeatable Sarasota lifestyle. It’s where nature, culture, and waterfront living converge right outside your door. Come experience yourself!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Barbara May (404-822-9264)
1621 PINE BAY DR, SARASOTA, FL 34231
$1,950,000154 Days on yellowkey MLS ID: A4663412
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 3201 Built: 1980Monthly Fee: $17 Tax: $15,556 (2024)Community: Johnson EstatesSingle Family
Taxes:$15,556
Remarks: On a lush one-third-acre homesite in desired Pine Bay Estates, this single-story residence has been entirely rebuilt and elevated through a comprehensive, design-forward renovation exceeding $1.1 million. The result is a serene coastal haven where timeless craftsmanship meets modern luxury. A full interior transformation opened the home to light, flow and functionality. The newly relocated chef’s kitchen features bespoke cabinetry, premium finishes and a full suite of Thermador appliances, all thoughtfully positioned to overlook the tropical gardens. Wide-plank flooring carries through every room, complemented by exposed beams, curated lighting and refined architectural details. Every major system has been replaced or upgraded, including all-new HVAC, a tankless water heater, new plumbing and water lines, new insulation, and hurricane-rated windows, doors and sliders, ensuring enduring comfort and peace of mind. The home’s heart is its stunning sunroom, surrounded by glass and bathed in natural light, an ideal space for morning coffee, quiet reading or gathering with guests while taking in the lush, mature landscaping. Three beautifully redesigned baths, a gas fireplace, custom California Closets and a new laundry suite continue the theme of thoughtful luxury throughout. Outside, the home lives like a private botanical retreat. A full landscape redesign brought in layered tropical plantings, ambient lighting, new walkways and hardscape, all-new fencing and gates, and a pool with a replaced deck and rescreened cage. A new roof, fresh stucco exterior, carport enhancements and upgraded exterior lighting, complete the transformation. With its rare combination of single-level living, expansive grounds and meticulous top-to-bottom renovation, this Pine Bay Estates residence offers an inspired West of Trail lifestyle just moments from Southside Village, Siesta Key and Sarasota’s finest dining, beaches and marinas.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Katy Mcbrayer (941-400-2406)
3512 CAMINO REAL, SARASOTA, FL 34239
$2,745,000162 Days on yellowkey MLS ID: A4671290
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3810 Built: 2025 Tax: $6,583 (2025)Community: GranadaSingle Family
Taxes:$6,583
Remarks: 3512 Camino Real represents a rare opportunity to acquire a newly constructed luxury residence strategically positioned for high-performing short-term rental income in one of Sarasota’s most supply-constrained residential corridors. Located inside the City of Sarasota and approximately 10 minutes to Siesta Key Beach, Siesta Key Village, and Downtown Sarasota, this property is purpose-built to operate under a weekly rental model that aligns with current city regulations while attracting higher-quality, longer-stay guests. Unlike many coastal investment properties that rely on nightly rental volatility or regulatory gray areas, this home offers a compliant, predictable income profile paired with strong long-term appreciation fundamentals. Completed in 2025 by award-winning Heritage Builders, the British West Indies–inspired residence spans 3,810 square feet on an oversized .27-acre corner double lot, offering 5 bedrooms, 4.5 bathrooms, a dedicated office, a game room, and a 3-car garage. The layout comfortably sleeps up to 12 guests, supporting premium weekly rates and strong demand across multiple seasons. The home’s interior and exterior amenities are intentionally aligned with today’s luxury short-term rental market: a private heated resort-style pool and spa, expansive covered lanai with outdoor kitchen, open-concept living areas, high ceilings, impact-rated windows, concrete block construction, and elevated hurricane standards. These features enhance guest experience while also reducing operational risk, insurance exposure, and long-term maintenance costs—key considerations for investor underwriting. From an operational standpoint, a weekly rental strategy delivers meaningful advantages: fewer guest turnovers, lower housekeeping and wear-and-tear costs, improved booking stability, and reduced party risk. The surrounding Granada neighborhood further strengthens the investment thesis, offering oak-lined sidewalks, walkable parks, proximity to boating access, Southside Village dining, and Downtown Sarasota’s cultural and marina district—all while remaining above the flood zone, a critical differentiator for long-term ownership and asset resilience. Beyond income potential, 3512 Camino Real offers multiple exit strategies. Its new-construction pedigree, desirable residential setting, and luxury finish level support future resale to primary residents, second-home buyers, or continued investor ownership. Limited supply of large, newly built homes with pools inside Sarasota city limits underpins long-term value appreciation and broad buyer appeal across market cycles. A comprehensive Short-Term Rental Investor Report, including projected revenue, operating assumptions, conservative and upside scenarios, and long-term investment analysis, is available upon request and is attached in the MLS for qualified buyers.
Listing is courtesy of: EXP REALTY LLC (800-486-1794)
Listing Agent: Mark Coppens (941-444-0436)
2475 BAY ST, SARASOTA, FL 34237
$2,012,00068 Days on yellowkey MLS ID: A4676732
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2874 Built: 2024 Tax: $14,004 (2025)Community: Hudson ParkSingle Family
Taxes:$14,004
Elementary School: Alta Vista Elementary
Remarks: Experience refined modern living at 2475 Bay Street, a brand-new contemporary residence offering 2,874 square feet of thoughtfully designed space. Clean architectural lines and a striking façade set the tone, while inside, sun-filled interiors reveal soaring ceilings, expansive open-concept living areas, and walls of glass that create a seamless indoor-outdoor connection. The home is designed to feel both elevated and livable, with spaces that flow naturally for entertaining, relaxing, and everyday life. The home features four bedrooms and four bathrooms, including a main-level primary suite that offers split-plan privacy and direct access to the pool area. The primary bath includes a double vanity, walk-in shower, soaking tub, and spacious his-and-hers closets with built-in accessories. The chef’s kitchen is outfitted with Café appliances accented in gold, premium cabinetry, Calcutta quartz countertops throughout the home, and a dramatic waterfall island seating eight. An upstairs living area overlooks the main level and opens to a second-story balcony, while additional bedrooms feature en-suite baths for comfort and privacy. Additional highlights include a custom resort-style pool, fully fenced yard, covered lanai with a fully equipped outdoor kitchen, two-car garage, energy-efficient construction, paver driveway accommodating up to four vehicles, and a mudroom with direct access to the pantry. Ideally located in central Sarasota, this home offers a peaceful residential setting with quick access to downtown and the area’s top attractions. Enjoy nearby Main Street dining, boutique shopping, and cultural venues such as the Sarasota Opera House, Florida Studio Theatre, and McCurdy’s Comedy Theatre. Outdoor and lifestyle destinations include Bayfront Park and Marina, Marie Selby Botanical Gardens, Payne Park, St. Armands Circle, Sarasota Jungle Gardens, The John and Mable Ringling Museum of Art, and Mote Marine Aquarium. World-renowned beaches including Siesta Key, Lido Key, and Longboat Key are just minutes away, along with convenient access to Publix, Sarasota Memorial Hospital, top schools, and Sarasota-Bradenton International Airport. Schedule your private tour and experience the design, flow, and lifestyle of this unique Sarasota property before it slips away.
Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)
Listing Agent: Desiree Doggett (941-900-6380)
2435 EUGENE ST, SARASOTA, FL 34231
$398,000110 Days on yellowkey MLS ID: A4676302
1 Days Off yellowkey (back on 4/4/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1170 Built: 1959 Tax: $3,021 (2025)Community: Pinehurst Park Rep OfSingle Family
Taxes:$3,021
Elementary School: Gulf Gate Elementary
Remarks: Under contract-accepting backup offers. Significant Price Improvement! Just 4.5 miles from the powdery white sands of Siesta Key Beach, this fully renovated Sarasota retreat delivers the freedom, style, and lifestyle buyers are craving — without HOA restrictions and with monthly rentals allowed. Renovated in 2025, this 2-bedroom, 2-bath block home blends modern design with effortless flow, creating a space that feels both elevated and inviting. The heart of the home is a show-stopping, European-inspired kitchen, thoughtfully designed with high-end cabinetry and a premium appliance package — perfect for casual mornings, entertaining friends, or unwinding after a beach day. The open-concept layout maximizes every inch of the 1,170 sq ft, offering seamless transitions between living, dining, and kitchen spaces. New flooring throughout and a completely updated bathroom add to the fresh, move-in-ready feel. Major upgrades provide peace of mind and long-term value, including: *BRAND NEW ROOF*--- *Hurricane-rated windows and doors*--- *Solid block construction*--- It is also Located in Flood Zone X Step outside to a fully fenced backyard designed for flexibility and Florida living. With room for a pool, a drive-through gate for easy boat or RV storage, an oversized driveway, and a large storage shed, this property offers a level of versatility rarely found this close to the coast. Set in a prime Sarasota location near Gulf Gate Library, popular dining, shopping, and neighborhood favorites — with quick access to Siesta Key, Downtown Sarasota, Downtown Sarasota, and surrounding hotspots — this home checks every box for a primary residence, investor, or lifestyle buyer seeking freedom and upside. Homes this close to Siesta Key with no deed restrictions, modern renovations, rental flexibility, and space for boats or RVs are exceptionally rare. Schedule your private showing today — opportunities like this don’t last.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-907-2000)
Listing Agent: Julie Shaw (941-408-4760)
1759 WALDEMERE ST, SARASOTA, FL 34239
$4,449,999193 Days on yellowkey MLS ID: A4666725
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4513 Built: 2025 Tax: $13,348 (2024)Community: Midwood ManorSingle Family
Taxes:$13,348
Remarks: One or more photo(s) has been virtually staged. West of Trail luxury meets modern innovation at 1759 Waldemere Street. This brand-new, custom-built residence embodies timeless design, contemporary craftsmanship, and intentional indoor–outdoor living. Set on a .33-acre lot just steps from Southside Village and Sarasota Memorial, the home delivers sophistication, convenience, and exceptional attention to detail in one of Sarasota’s most sought-after neighborhoods — a rare opportunity in the coveted West of Trail community. Spanning 4,513 square feet, the two-story floor plan features four bedrooms, five baths, an office with private entry, and a media room that opens to a 480-square-foot balcony overlooking the property. Designed for both everyday living and elegant entertaining, the home showcases expansive sliding glass doors that blur the line between indoors and out, opening to a heated saltwater pool, spa, and lush landscaped backyard for year-round enjoyment. The designer kitchen serves as the heart of the home, featuring Sub-Zero and Wolf appliances, custom cabinetry, imported stone, and a hidden butler’s pantry. The first-floor primary suite epitomizes luxury with zero-corner sliders that open directly to the pool and outdoor living area. Inside, a spa-inspired bath includes a freestanding tub, walk-in shower, and a custom built-in walk-in closet. Upstairs, two en suite bedrooms and a second-floor primary suite give privacy for family or guests. A versatile media room and expansive outdoor terrace complete the level, overlooking the serene backyard oasis. Every detail has been thoughtfully curated — from the bespoke, locally handcrafted Sapele wood entry door to hurricane-impact windows and doors, a three-car garage with epoxy flooring, and professional landscaping surrounding the fenced backyard. Ideally located in the highly regarded Southside Elementary School district, near Sarasota Memorial Hospital and the shops and dining of Southside Village, with downtown Sarasota, Siesta Key, Lido Key, and St. Armands Circle just minutes away. This is more than a home — it’s a statement of Sarasota luxury living.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Rachel Hamrick (941-529-1773)
6338 BEECHWOOD AVE, SARASOTA, FL 34231
$589,00037 Days on yellowkey MLS ID: A4685783
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1506 Built: 1954 Tax: $1,942 (2025)Community: Emerald HarborSingle Family
Taxes:$1,942
Remarks: Located less than a mile from the world-famous Siesta Key Beach, this charming 3-bedroom, 2-bathroom home offers the perfect blend of coastal living and everyday convenience. Situated on a spacious lot, the property features a large backyard—ideal for outdoor entertaining, gardening, or simply enjoying Florida’s beautiful weather. A separate shed in the backyard provides additional storage or workspace. Hurricane windows throughout the house as well as an updated AC. Enjoy being just minutes from shopping, restaurants, and entertainment, while still tucked away in a quiet residential setting. Take a relaxing walk or short bike ride to the beach and experience the stunning white quartz sand and breathtaking sunsets that make Siesta Key so special. Whether you’re looking for a primary residence, vacation getaway, or investment opportunity, this home offers endless potential in one of Sarasota’s most desirable locations.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Maryana Zilinskiy (941-744-6065)
2639 BOUGAINVILLEA ST, SARASOTA, FL 34239
$864,00064 Days on yellowkey MLS ID: A4681333
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2435 Built: 1960Monthly Fee: $17 Tax: $8,234 (2025)Community: South GateSingle Family
Taxes:$8,234
Remarks: Enjoy life to the fullest in this 3 bedroom, 3 bath mid-century modern style ranch home, nestled on a near 1/3 acre lot in the sought-after South Gate neighborhood, offering over 2,400 square feet of architecturally updated and meticulously maintained living space. From the moment you arrive, this private sanctuary impresses with iconic palm trees, a custom circular paver driveway, professionally lit landscaping, and a vivid one-of-a-kind patio with a colorful front entry. Inside, the light and bright open-concept floorplan showcases flawless terrazzo flooring and a striking modern contrasted kitchen with stainless steel appliances and a large island with bar-top seating. The kitchen and living areas flow seamlessly into the family and dining room, providing ample gathering space and an entertainment center ready for modern electronics. French doors lead to an almost 40-foot screened lanai overlooking a professionally manicured, fenced, and irrigated backyard accented with coping. The primary bedroom features a private exterior entrance, space for a desk or seating area, and an en-suite bath with a walk-in closet with built-in shelving and safe, a wall-to-wall glass shower with multiple massage jets and bench seating, and a separate water closet. Two additional contemporary bedrooms and bathrooms are located on the opposite side of the home. The remodeled two-car garage is climate controlled and includes a full laundry room with utility sink. Major upgrades and systems include a standing seam metal roof, hurricane-rated impact windows and garage door, tankless water heater, whole-home generator, updated electrical system with new controls, and a plumbing system rerouted with exterior clean-outs for easy access. The home includes both a 100-gallon and 500-gallon propane tank, with the generator operating from the 500-gallon tank and the water heater capable of running from either tank, all serviced on a regular basis. Indoor comfort is enhanced by a professionally maintained HVAC system with in-duct air purification, including UV lighting and a whole-home purification system. Smart-home features allow remote control of the irrigation system, HVAC, alarm system, front door lock, and security cameras. The driveway has been recently resealed, and exterior security lighting surrounds the home. Optional membership to the South Gate Community Association offers social activities and pool access at the historic community center for a nominal fee. Ideally located just minutes to golf courses, boat clubs, Downtown Sarasota dining, shopping, nightlife, cultural events, and the world-famous beaches of Siesta Key.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Alan Macloughlin (941-780-8628)
5201 AVENIDA DEL MARE, SARASOTA, FL 34242
$1,495,00073 Days on yellowkey MLS ID: A4680975
REDUCED by $65,000 (4.2%) on 04/01/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2802 Built: 2008 Tax: $6,145 (2025)Community: Sarasota BeachSingle Family
Taxes:$6,145
Remarks: WELCOME to one of Siesta Key's hidden gems. From this Key West style home, you can walk or bike ride to the soft, quartz sands of Siesta Beach or the quaint Siesta Village in minutes. This exceptional home offers high end finishes throughout. The native yard features beach sunflowers and other native plants and shrubs. The front door entrance invites you into the main level with an easy flow between the living room and the dining room. The gourmet kitchen features wood cabinets, granite countertops, stainless steel appliances and French Door refrigerator. The guest bath, laundry room and bonus room complete the downstairs. The backyard is a fenced, private oasis with a pool surrounded by stone pavers with room for lounge chairs, grill and an outdoor table setting. Mature royal palm trees and smaller palms create a beautiful habitat for birds and other wildlife. The second floor has two comfortable bedrooms, one with a private balcony. A full bath completes this level. The top level offers a spacious Primary Bedroom and En Suite Bathroom retreat with exceptional amenities, a large bathroom with granite countertops, wrap-around walk-in shower, and separate garden tub, with a screened-in balcony overlooking the pool area. The top level is completed by an additional Bedroom with an en suite Bathroom with walk-in shower, linen closet, and granite countertops. Additional features include solar panels (paid in full), a security system, stone paved driveway and walkway, along with an oversized 2 car garage. This open, sunny home is located in a quiet neighborhood at the end of the street and has so many quality features. It is definitely worth a visit.
Listing Agent: Mary Kassen (941-900-9776)
2904 HOMASASSA RD, SARASOTA, FL 34239
$595,00054 Days on yellowkey MLS ID: A4683642
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1562 Built: 1964 Tax: $5,896 (2025)Community: South GateSingle Family
Taxes:$5,896
Elementary School: None
Remarks: 3 Bed | 2 Bath | Pool Home | Fully Furnished | Updated Kitchen | Investment Opportunity***Welcome to your perfect Sarasota retreat! This beautifully maintained 3-bedroom, 2-bath pool home offers comfort, style, and an unbeatable location — ideal as a private residence, vacation home, or income-producing investment property.***The home features a recently updated kitchen with new cabinetry and quartz countertops, providing a modern, stylish space for everyday living and entertaining. Offered fully furnished, this property is truly turnkey for immediate occupancy or rental use.***Step outside to your private backyard oasis featuring a sparkling pool and inviting fire pit area — perfect for relaxing or hosting guests in a peaceful Florida setting.****Prime Location> Minutes to Sarasota Memorial Hospital,>Near Sarasota’s vibrant cultural downtown district,>Only 10 minutes to Siesta Key Beach — ranked #1 in the USA for its world-famous quartz sand,>Close to top restaurants, shopping, and entertainment**** Property Highlights>3 bedrooms / 2 bathrooms,>Recently updated kitchen with new cabinets & quartz countertops,>Private pool with fire pit entertainment area,>Fully furnished — move-in or rent ready,>Excellent as primary home, vacation property, or rental investment,>Strong income potential in a high-demand location. Experience the best of Sarasota living with world-class beaches, dining, and lifestyle just minutes away. And find out for your self, "What's all the fuss about Sarasota"
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Tracy Srodes (813-267-1312)
8701 MIDNIGHT PASS RD #106A, SARASOTA, FL 34242
$595,000184 Days on yellowkey MLS ID: A4668247
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1357 Built: 1980 Tax: $7,433 (2024)Community: Turtle Bay Sec 2Condo
Taxes:$7,433
Remarks: PRICE ADJUSTMENT!! Motivated sellers, seller financing will be considered! Turtle Bay community has a 3-month minimum rental policy. Experience the best of Siesta Key in this beautifully unfurnished 2BR/2BA condo in the highly desirable Turtle Bay community. Enjoy breathtaking views of Little Sarasota Bay from the enclosed, screened lanai, ideal for relaxing mornings or evening breezes. The remodeled kitchen features stainless steel appliances, updated quartz countertops, and a breakfast bar that opens into the spacious, open-concept living and dining area, perfect for entertaining. The primary suite offers an updated en-suite bathroom, walk-in closet, and built-in vanity. The generously sized second bedroom is perfect for guests or a home office. Additional conveniences include an in-unit laundry room. Recent updates include a 2023 2.5-ton Trane HVAC unit, renovated bathrooms, LED recessed lighting, and popcorn ceiling removed. A rare 12x22 detached end-unit garage provides excellent storage for your vehicle, bikes, or beach and boating gear. Turtle Bay offers resort-style amenities, including a heated pool, hot tub, clubhouse, onsite management, tennis and pickleball courts, lush landscaping, newly updated fishing pier, and boat docks - boat slips are available for nominal fee on a first-come, first-served basis. Milestone Inspection has been completed for the new owner's piece of mind. Enjoy easy access to the sparkling Gulf of Mexico waters with deeded beach access just across the street via the Tortuga Community. Conveniently close to Siesta Key Village and Siesta Key Public Beach via the free trolley stop just steps away. Coastal living at its finest! Schedule your showing today!
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Justin Piccillo (908-670-3209)
6308 MIDNIGHT PASS RD #6, SARASOTA, FL 34242
$995,000290 Days on yellowkey MLS ID: A4657483
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1232 Built: 1965Monthly Fee: $1,005 Tax: $5,582 (2025)Community: Crescent ArmsVilla
Taxes:$5,582
Remarks: Coastal Luxury Villa with Thai-Inspired Elegance Now Offered at $995,000 Experience the best of Siesta Key living in this beautifully renovated two-bedroom, two-bath villa located in the highly sought-after, gated beachfront community of Crescent Arms. Now priced at $995,000, this is a compelling opportunity recently adjusted from $1,075,000 to reflect today’s market and create immediate value. This thoughtfully updated residence blends custom coastal finishes with subtle Thai-inspired design, creating a warm, serene atmosphere throughout. The open-concept layout offers seamless flow between the kitchen, dining, and living areas ideal for both everyday living and entertaining. The gourmet kitchen features quartz countertops, stainless steel appliances, and generous workspace, all opening into a bright and inviting living area. Both bathrooms have been tastefully updated with spa-like finishes, including a walk-in shower and modern fixtures. Step outside to your private patio perfect for relaxing, grilling, or enjoying the tropical surroundings just moments from the beach. Crescent Arms offers exclusive private beach access to world-famous Siesta Key Beach, along with onsite management making this an excellent option for personal use, vacation rental income, or a combination of both. This property has a proven rental history with strong year-round bookings. Whether you’re searching for a coastal retreat, investment opportunity, or both, this villa delivers location, lifestyle, and value. Sold turnkey move right in or start generating income immediately.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Derek Edwards (941-929-3183)
2438 WISTERIA ST, SARASOTA, FL 34239
$750,00065 Days on yellowkey MLS ID: A4682306
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1317 Built: 1962 Tax: $8,476 (2025)Community: South GateSingle Family
Taxes:$8,476
Remarks: Welcome to 2438 Wisteria St. This turnkey property is ready for YOU, located in the desirable Arlington Park neighborhood. Everything can be included in this purchase! New roof in 2025, new pool in 2022, fresh landscaping, along with all the recent updates inside this home, make this a move-in ready home! This property boasts an impressive rental history as well, just ask! Listed as a 2 bedroom home, but it has an extra room that could be used as a 3rd bedroom or office space! This home offers an open floorplan, galley style kitchen that has been updated, and features a cozy breakfast nook. The view from the spacious living room looks out to the back yard, while first housing a bright and airy sunroom. Make your way to the back yard and you will find yourself in your own resort style oasis! The beautiful pool is the star of the back yard! There's a large paved patio, as well as a spacious turf area, with a hammock and swings, for the ultimate relaxation retreat. Brand NEW Aquavoss cold plunge/hot tub! You won’t want to leave! This home is Located conveniently near downtown Sarasota, with its world-famous beaches, dining, shopping, and luxurious lifestyle this amazing town offers!
Listing Agent: Nic Yoder (941-993-9268)
6518 MIDNIGHT PASS RD #310, SARASOTA, FL 34242
$899,000124 Days on yellowkey MLS ID: A4675259
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1215 Built: 1975 Tax: $7,724 (2025)Community: House SunCondo
Taxes:$7,724
Remarks: Reduced 30K! The Best Views Currently Available at House of the Sun! Rarely available 3rd-floor unit in the always desirable and impeccably managed House of the Sun on Siesta Key. Positioned far forward on the north side of the building, this residence enjoys some of the best Gulf and beach views currently on the market. From both the living room and the lanai, take in sweeping views of the Gulf and Siesta Key’s world-famous white sand beach. House of the Sun offers 100 feet of direct beachfront and an exceptional location just 500 feet south of the Stickney Point Bridge, providing quick and easy access to and from the mainland. The property is also within walking distance of a wide variety of restaurants, clubs, and everyday conveniences including gourmet food and fish markets, coffee and ice cream shops, liquor store, clothing and gift shops, salons, postal and shipping services, and beach, sport, and boat rentals. Popular local favorites such as Captain Curt’s and Daiquiri Deck are just steps away. This unit has seen significant recent updates (2023–2025) including new hurricane-impact sliding glass doors and bedroom windows, a new rooftop A/C system, fresh interior paint in common areas, and new LVT flooring throughout the living areas and bedrooms. The kitchen has been upgraded with new stainless steel appliances, and additional improvements include a new master bedroom mattress, window shades, rugs, and bedding. Additional features include an in-unit washer and dryer, owner’s closet, and under-building parking. House of the Sun has also undergone extensive common-area improvements (2024–2025), including new elevators, a new hurricane-impact roof, updated pool and tennis court, enhanced pool-area common room with new exercise equipment, new gas grill stations, refreshed outdoor seating areas, landscaping, hallway paint, carpet, lighting, and upgraded Wi-Fi throughout the building. The complex is pet-friendly for owners and is known for having one of the best-run on-site rental programs on Siesta Key, offering a three-night minimum rental policy. This unit performed well in its first year in the rental pool and offers an excellent balance of personal enjoyment and rental income potential. Sale subject to future bookings.
Listing is courtesy of: TIDELINE REAL ESTATE BROKERS (941-587-1669)
Listing Agent: Mike Winger (941-228-3390)
1904 MONTE CARLO DR #1102, SARASOTA, FL 34231
$585,000143 Days on yellowkey MLS ID: A4672726
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 1745 Built: 2021 Tax: $6,828 (2024)Community: Phillippi Lndgs CCondo
Taxes:$6,828
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Discover elevated waterfront living in the prestigious gated community of Phillippi Landings, where this beautifully updated 4-bedroom, 3-bath residence offers an exceptional blend of privacy, comfort, and coastal elegance just moments from the world-renowned shores of Siesta Key. This refined home features spacious light-filled interiors, luxury flooring, and designer finishes throughout, enhanced by the convenience of a private in-unit elevator and a whole-home water filtration system. The gourmet kitchen showcases premium appliances, stone countertops, custom cabinetry, and a generous island perfect for gathering and entertaining. The serene primary suite offers spa-inspired finishes and impressive closet space, while three additional bedrooms provide versatility for guests, an office, fitness room, or multi-generational living. The screened lanai invites year-round indoor-outdoor enjoyment overlooking lush landscaping. Additional perks include parking for three vehicles along with ample guest parking. Residents of Phillippi Landings enjoy resort-style amenities including a heated pool and spa, fitness center, clubhouse, dog park, gated entry, walking paths, kayak and paddleboard launch, and access to marina-style docks along the Intracoastal Waterway. Ideally located near Siesta Key Beach, Downtown Sarasota, Gulf Gate, top dining, shopping, marinas, medical centers, and Sarasota’s renowned cultural attractions, this residence offers an exceptional coastal lifestyle in one of Sarasota’s most desirable waterfront communities.
Listing Agent: Katie Cobb (913-744-0248)
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