Location: Sarasota
Keyword(s): Sarasota High
Keyword(s) High School: Sarasota High
Do Not Show Listings
5838 ELEGANT ORCHID WAY, SARASOTA, FL 34232
$445,0007 Days on yellowkey MLS ID: A4694819
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1494 Built: 2020Monthly Fee: $81 Tax: $2,853 (2025)Community: Garden Village Ph 3ASingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,853
Elementary School: Ashton Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: McIntosh Middle
Remarks: Welcome to this appealing 3-bedroom, 2-bath single-family home located in Garden Village, one of the most affordable gated communities in the area, conveniently located near Cattlemen Road, Fruitville Road, and I-75 (Exit 210). This one-story, all-concrete-block home includes a 2-car garage and a fully fenced backyard. Its open-concept layout maximizes living space, with the kitchen positioned between the living area and dining room. The kitchen overlooks the living area and covered lanai and comes equipped with all major appliances, including a refrigerator, built-in dishwasher, electric range, and microwave. The laundry room also includes a washer and dryer. For added privacy, the owner's suite is located at the back of the home and features an ensuite bathroom. Two additional bedrooms share a second full bathroom. Garden Village offers a convenient location just 30 minutes from Siesta Key Beach and 15 minutes from UTC (University Town Center), as well as the newly opened Mote Science Education Aquarium.
Listing is courtesy of: ROSEBAY INTERNATIONAL REALTY, INC (941-366-7673)
Listing Agent: Ray Shope (941-321-1328)
2564 WOOD ST, SARASOTA, FL 34237
$449,00020 Days on yellowkey MLS ID: A4693167
REDUCED by $1,000 (0.2%) on 05/27/2026
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 2118 Built: 1958 Tax: $5,488 (2025)Community: Hudson ParkApartment
Taxes:$5,488
Elementary School: Alta Vista Elementary
Middle School: Brookside Middle
Remarks: A Rare Find in the Heart of Sarasota — Two Homes, One Exceptional Opportunity In a city where inventory is tight and opportunities like this surface only once in a while, this dual-unit property stands apart. Whether you're an investor chasing cash flow, a family seeking connected-but-separate living, or a homeowner looking to let rental income offset your mortgage — this is the one. The Main Home is warm and welcoming, with two bedrooms, a full bath, and a den that adapts to whatever life demands — home office, reading room, guest space. The eat-in kitchen keeps things bright and functional, and the screened lanai is your front-row seat to everything that makes Florida living worth it. A covered carport, plus shared laundry just steps away, keeps daily life effortless. The Rear Dwelling operates as a fully independent two-story residence — its own driveway, its own entrance, its own world. Two bedrooms, one bath, and a smart layout split across two floors give tenants or family members the privacy they want without sacrificing connection to you. And when you're not relaxing on the lanai? You're minutes from Sarasota's celebrated dining and arts scene, the Legacy Trail, and some of the most beautiful beaches on the Gulf Coast — Siesta Key, Lido Key, all within easy reach. Extra storage on site fits a boat, trailer, or RV. Because why not? Two units. Endless possibilities. One showing to change everything.
Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)
Listing Agent: Aaron Wittenstein (941-299-1151)
3763 KOSTEN PL, SARASOTA, FL 34240
$362,50019 Days on yellowkey MLS ID: A4693472
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1654 Built: 1961 Tax: $1,296 (2025)Community: Golf Club EstatesSpa: NoSingle Family
Taxes:$1,296
Elementary School: Tatum Ridge Elementary
Remarks: This spacious 3-bedroom, 2-bath home with an additional bonus room that was the former garage, is packed with potential and ready for its next chapter! Situated in Golf Club Estates, this property being sold “as-is” offers a fantastic opportunity for investors, renovators, or buyers looking to customize a home to their own style and vision. Featuring a newer roof installed just 2 years ago, one of the major big-ticket items has already been completed, giving peace of mind for future improvements. Inside, the home remains in original condition and is ready for updating, but it offers a solid foundation, functional layout, and “good bones” that make it an ideal renovation project. The home’s layout provides endless possibilities for redesigning and modernization while preserving its character. Whether you’re searching for your next investment property, a fix-and-flip opportunity, rental potential, or a chance to create your dream home with sweat equity, this property delivers incredible upside. With strong structural potential, ample living space, and the costly roof replacement already behind you, this home is the perfect canvas to bring your ideas to life. Don’t miss this rare opportunity to unlock the value and possibilities this property has to offer!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Chris Jeanes (941-330-4844)
916 PATTISON AVE, SARASOTA, FL 34237
$409,00018 Days on yellowkey MLS ID: A4693771
REDUCED by $11,000 (2.6%) on 05/26/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1044 Built: 1961 Tax: $4,185 (2025)Community: Robin Hood WoodsSpa: NoSingle Family
Taxes:$4,185
Remarks: Don't let this one pass you by. Tucked in one of Sarasota's most sought-after locations, this beautifully updated single-family home offers the perfect blend of timeless neighborhood charm, modern comfort, and an active lifestyle — with no HOA to slow you down. Inside, a fully remodeled kitchen showcases quartz countertops, stainless steel appliances, and custom cabinetry, while two tastefully renovated bathrooms reflect the same attention to detail and designer touch found throughout. Natural light pours through the open layout, creating a warm, inviting atmosphere whether you're entertaining guests or simply settling in after a day at the beach. The big-ticket work is already behind you. A newer roof, updated HVAC, plumbing, and electrical mean you're stepping into genuine peace of mind — not a project. Outside, a spacious screened lanai and fenced backyard invite you to slow down, let the pets roam, tend the garden, or simply enjoy a warm Gulf evening in complete privacy. All of this, just minutes from the energy of downtown Sarasota — world-class dining, boutique shopping, pristine parks, and the Gulf's most celebrated beaches, world-renowned Yoders Marketplace, or a quick trip to the UTC area for outstanding retailers, Mote Marine, parks, walking trails, and more. Whether you're planning your starter home, escaping the winters, or adding a smart investment to your portfolio, this home checks every box. Stylish. Updated. Move-in ready. This is Sarasota living at its finest. Call today for your personal tour.
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Kathleen Long (813-470-0047)
6415 MIDNIGHT PASS RD #211, SARASOTA, FL 34242
$849,900166 Days on yellowkey MLS ID: A4675481
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2358 Built: 1975 Tax: $7,544 (2025)Community: AnchorageSpa: NoCondo
Taxes:$7,544
Elementary School: Phillippi Shores Elementary
Remarks: Deeded beach access, Intracoastal waterway frontage with boat dockage AND room for the whole family! Discover the epitome of coastal living in this fabulous three-bedroom, two-and-a-half-bath residence, boasting 2,358 square feet of interior space and an expansive balcony spanning the entire length of the home. Recently upgraded with $80,000 worth of high-impact hurricane sliders, the spacious floor plan offers multiple living and dining areas, with a split layout ensuring privacy. This is a real gem for investors as it is one of only eight 3-bedroom units in the building. At the Anchorage, owners and renters enjoy deeded, gated beach access right across the street, a canal with boat dockage and kayak/paddleboard launch, and beautiful sprawling park-like grounds overlooking the intracoastal waterway. Other amenities include a gated entrance, heated pool, fitness center, clubhouse, tennis and pickleball courts, shuffleboard courts and kayak racks. Onsite rental management and a one-week minimum rental make this community very popular with vacationers and savvy investors alike. Come see why The Anchorage is the place to be year-round on Siesta Key.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Mina Johnson (941-404-9347)
1035 SEASIDE DR #308, SARASOTA, FL 34242
$2,600,00028 Days on yellowkey MLS ID: A4692379
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1646 Built: 2023 Tax: $21,387 (2025)Community: Ten35 SeasideSpa: YesCondo
Taxes:$21,387
Middle School: Sarasota Middle
Remarks: Gulf-Front Luxury with Investment Appeal Experience elevated beachfront living at Ten35 Seaside, a boutique Gulf-front community on the quiet southern end of Siesta Key. This beautifully designed 2-bedroom, 2.5-bath residence offers private beach access, resort-style amenities, and strong luxury rental potential. The open-concept layout features Wolf and Sub-Zero appliances, custom cabinetry, sleek coastal finishes, and spacious living areas filled with natural light. Sliding glass doors open to a private terrace perfect for enjoying Gulf breezes and sunset skies. The primary suite offers a spa-style bath and walk-in closet, while the guest suite includes built-in bunk beds for added flexibility and rental appeal. Residents enjoy a beachfront pool and spa, private cabanas, fitness center, and direct access to Siesta Key’s world-famous beaches — all just minutes from Siesta Key Village and downtown Sarasota. Ideal as a luxury beachfront retreat, full-time residence, or income-producing coastal investment property. Buyer to verify rental policies, restrictions, and all room dimensions.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Rex Glasson (941-587-6135)
5300 OCEAN BLVD #202, SARASOTA, FL 34242
$1,130,000138 Days on yellowkey MLS ID: A4678274
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1372 Built: 1973 Tax: $9,941 (2025)Community: Terrace EastCondo
Taxes:$9,941
Remarks: 65 steps to the sand, 312 steps to the water from the Terrace East property are waiting for you! Walk inside and unwind in this updated, turnkey luxury condominium offering nightly sunset views of the #1 beach in the country. This is a rare opportunity to own a condominium in the vibrant heart of Siesta Key, walk to all the amenities and charm that Siesta Key village offers. The property is just steps from the world-famous quartz sands of Siesta Key Beach. Tastefully decorated and truly move in ready, this coastal retreat features a beautifully updated kitchen with custom cabinetry, granite countertops, tile backsplash, stainless steel appliances, crown molding, and thoughtful designer finishes. Luxury vinyl flooring flows throughout the condominium, creating a cohesive and low maintenance living space ideal for beachside living. Both bathrooms have been updated and showcase tile showers with elegant quartz sinks. Two spacious balconies provide the perfect setting to enjoy stunning Gulf sunsets, entertain family and friends, or take in the vibrant island atmosphere below. The island lifestyle is at your doorstep with easy access to local restaurants, live music, boutique shopping, and even a grocery store within .2 of a mile. Located in the iconic Terrace East, this 24-hour secure building offers a welcoming common area for residents and guests. The community has recently enhanced its curb appeal with updated landscaping and beautifully refreshed grounds, creating a true resort style ambiance. Residents enjoy a spacious sparkling pool with new pool furniture, an exercise room, a private tennis/pickleball court, and new stainless steel outdoor grills perfect for entertaining. Whether you are searching for a primary residence, second home, or vacation getaway, this condominium delivers luxury, comfort, and exceptional walkability in one of Florida’s most desirable beach destinations. Experience the best of Siesta Key beach lifestyle in an elevated retreat that combines iconic location, modern updates, and outstanding amenities.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Diane Goodwin (941-706-6620)
3099 DICK WILSON DR, SARASOTA, FL 34240
$1,725,000166 Days on yellowkey MLS ID: A4673663
REDUCED by $100,000 (5.5%) on 05/27/2026
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 4069 Built: 1990Monthly Fee: $369 Tax: $7,352 (2024)Community: Laurel Oak EstatesSpa: NoSingle Family
Taxes:$7,352
Tax Year: 2024
Remarks: This is the one * WELCOME TO LAUREL OAK ESTATES & COUNTRY CLUB, ONE OF THE MOST COVETED COUNTRY CLUB COMMUNITIES IN SARASOTA * This EXECUTIVE HOME BOASTS PANORAMIC VIEWS of a LARGE LAKE & GOLF COURSE * These are MUST SEE VIEWS * A very private setting that is perfectly positioned on OVER 1/2 ACRE * PRIDE OF OWNERSHIP SHOWS * Featuring 3 SPACIOUS Bedrooms & 3 Full Baths PLUS a Den/Office * Split Plan Design * Formal Living Room with BEAUTIFUL COFFERED CEILING * The Chef's Kitchen is stunning showcasing Double Ovens , Cook-top Island, GORGEOUS STONE Counter-tops, and ample storage * The Kitchen is open to the Family Room featuring a Wood-burning Fireplace * The Primary Suite is a true retreat with a Spa-style Bath * All of this wraps your OUTDOOR LIVING SPACE with a Panoramic Pool Cage for your Heated Pool * There are TWO Covered Lanais with a Summer Kitchen + Vented Grill * LARGE, open Backyard * Breathtaking custom landscaping throughout the property * OVERSIZED 2 Car Garage with a Separate Golf Cart Garage * This is a SPECTACULAR home with INCREDIBLE curb appeal + a classic circular driveway * Tile Roof is 8 years young * A/Cs are zoned, 3 years young & 9 years young * Volume Ceilings * 8 foot Sliding Glass Doors * This is the perfect home for entertaining or simply relaxing in your slice of paradise * A special opportunity behind the gates of Laurel Oak Estates, an outstanding Country Club community where nature and elegance abound. Offering 800+ acres of beauty and serenity, it is easy to see why some of the most discerning homeowners call Laurel Oak home. Optional club with outstanding facilities including 2 championship courses, 12 Har-Tru tennis courts, Junior Olympic-sized heated pool, & beautiful clubhouse, golf shop and attended locker rooms. Enjoy reciprocity with the Bird Key Yacht Club (boating, tennis, fitness, dining & social events) and quick easy access to I75, downtown, UTC Mall, World Famous Siesta Key beach and our other beautiful beaches * Golf is optional, but if you want a golf membership, BUY THIS HOME AND GO TO THE FRONT OF THE LINE FOR A GOLF MEMBERSHIP. One look & you'll fall in love *
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Ryan Brown (941-330-7774)
4822 OCEAN BLVD #3D, SARASOTA, FL 34242
$825,00013 Days on yellowkey MLS ID: O6406435
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1440 Built: 1973Monthly Fee: $1,667 Tax: $3,838 (2025)Community: Siesta TowersSpa: NoCondo
Taxes:$3,838
Middle School: Booker Middle
Remarks: This condominium at Siesta Towers offers two master suites. Welcome to this extraordinary living experience and location where every day you can enjoy the gulf views and the palm trees dotting the horizon. Swim and relax in the heated outdoor pool that sits right on the waterfront. Enjoy a drink on the cocktail pier while you watch the dolphins swim or bask in the glowing light of the stunning sunsets. Includes gym, fishing pier, BBQ, club house, and bike storage. Located on Siesta Key on the water, close to public beach access and Siesta Key Village. Many local beaches, parks, nature preserves, and bird sanctuary's close by. This turnkey fully furnished condo offers serene personal space, ample storage, walk in closet, lots of natural light, brand-new hurricane doors, eat in kitchen, dining room, living room, and office area. Designated parking space.
Listing is courtesy of: HOUWZER INC (267-765-2080)
Listing Agent: Daniel Robinson (904-447-8922)
1640 WALDEMERE ST, SARASOTA, FL 34239
$6,450,00086 Days on yellowkey MLS ID: A4685215
INCREASED by $50,000 (0.8%) on 05/27/2026
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 5270 Built: 2026 Tax: $8,031 (2026)Community: Lewis Combs SubSpa: YesSingle Family
Taxes:$8,031
Elementary School: Southside Elementary
Tax Year: 2026
Remarks: Almost finished!!! Completion 3 weeks!!! Touch-ups and Staging in process now. Modern Luxury Villa | 1640 Waldemere St Experience the pinnacle of Gulf Coast luxury in this stunning Miami-style modern villa, perfectly situated West of Trail in one of Sarasota’s most coveted neighborhoods. This architectural marvel blends high-end technology with effortless coastal living, offering a sanctuary just minutes from the vibrant pulse of Downtown Sarasota and the world-renowned sands of Siesta Key and Lido Beach. The Residence Designed for the connoisseur of fine living, this home boasts a sleek, minimalist aesthetic defined by clean lines and expansive glass. Elevated Living: Move effortlessly between floors with your private elevator. The Great Indoors/Outdoors: Massive automated glass doors disappear to create a seamless transition to the resort-style pool deck, perfect for year-round entertaining. Privacy at Your Fingertips: Equipped with cutting-edge Smart Glass technology, windows transition from transparent to opaque instantly for ultimate privacy. Space for Everything: Featuring 5 spacious bedrooms, a dedicated executive office, and a private home gym, there is no better lifestyle or utility. Tech-Forward Luxury This is a fully realized Smart Home, designed for total control and ambiance: Integrated Smart Home System: Control lighting, climate, and security from your device. Whole-Home Audio: An immersive sound system flows through every room and out to the pool deck. Modern Finishes: Premium materials and high-end fixtures throughout reflect a commitment to quality and contemporary style. The Location Located West of 41, 1640 Waldemere St places you in the heart of Sarasota’s most desirable "West of Trail" district. You are seconds away from: Sarasota Memorial Hospital and the medical district. Downtown Sarasota’s fine dining, opera, and boutiques. St. Armands Circle and local beautiful sand beaches. Live the Future of Luxury. This villa isn't just a home; it’s a statement. Call for all details…
Listing is courtesy of: JOSEPH RUSSO, LICENSED R.E. BROKER (941-928-1613)
Listing Agent: Joseph Russo (941-928-1613)
2572 JEFFERSON CIR, SARASOTA, FL 34239
$749,00018 Days on yellowkey MLS ID: A4693524
REDUCED by $26,000 (3.4%) on 05/27/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1434 Built: 1972 Tax: $6,795 (2025)Community: South GateSpa: NoSingle Family
Taxes:$6,795
Remarks: This TURN-KEY sought-after CITY LIMITS gem is situated on a large 0.22 acre lot with an oversized 1 stall garage! Step inside this beach inspired, open concept beauty that is filled with natural Southern exposed light. Luxury vinyl flooring flows throughout, while the well-appointed kitchen features quartz countertops and stainless steel appliances, perfect for both everyday living and entertaining. The French doors invite you to a private fenced backyard retreat that boasts a new heated sun-shelf pool with an expansive paver deck to lounge. Recent updates provide you with peace of mind! Accordion shutters and a new electrical service have been installed. No cast iron here! Plumbing and supply lines have been replaced! Weekly rentals are allowed so don't miss this TURN-KEY opportunity within the City Limits! This home serves as the prime gateway to a vibrant, active lifestyle with a wide array of local amenities right at your fingertips! Arlington Park's walking trails, basketball, tennis, outdoor fitness stations, and the aquatic center are all within half a mile! The beaches, downtown, arts, dining scene and highly rated schools are only minutes away – all within one of the most desirable City limit’s neighborhoods, and no HOA fees!!!
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Kari Klein (941-961-7419)
409 N WASHINGTON DR, SARASOTA, FL 34236
$1,690,00014 Days on yellowkey MLS ID: A4693984
1 Days Off yellowkey (back on 5/26/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1682 Built: 1952 Tax: $11,959 (2025)Community: Saint Armands Div John Ringling EstatesSingle Family
Taxes:$11,959
Remarks: What if you could own a fully renovated beach house on St. Armands Circle for the price many buyers are paying for an outdated condo… while being surrounded by $3M-$10M homes just blocks from the Gulf? Welcome to 409 N Washington Drive, an exceptionally rare opportunity to own one of the least expensive fully renovated homes to become available on St. Armands in years. Perfectly positioned just two blocks from the world-famous boutiques, restaurants, and cafés of St. Armands Circle, and only three blocks from the beautiful beaches of Lido Key, this charming single-story bungalow captures the kind of lifestyle most only experience on vacation. And here, vacation never has to end. Tucked away on one of the quietest streets on the Key, this beautifully updated 2-bed, 2-bath residence spans about 1700 SF and has been thoughtfully designed to deliver effortless coastal living with a resort-style feel. Lush tropical landscaping creates a sense of privacy rarely found this close to the beach and Circle, while multiple outdoor patios, lounging areas, and a sparkling resort-style pool invite year-round indoor-outdoor living and entertaining. Behind the charming exterior is a completely updated residence designed for effortless ownership, low-maintenance living, and maximum enjoyment. The home has undergone extensive renovations including updated PVC plumbing, updated electrical systems, hurricane-rated impact windows and doors, renovated kitchen and bathrooms, upgraded flooring, modern finishes, updated appliances, and refreshed indoor-outdoor living spaces. Every detail was intentionally curated to create a bright, inviting atmosphere that feels relaxed, elevated, and move-in ready from day one. Unlike many older island properties that become renovation projects disguised as opportunities, 409 N Washington removes the uncertainty, expense, and disruption buyers often fear when purchasing near the coast. There is no looming “what will break next?” anxiety here. The heavy lifting has already been done. For investors, this property checks nearly every box that drives premium short-term rental performance: an iconic walkable location, proximity to the beach, strong luxury rental demand, a fully furnished turnkey setup, and a proven St. Armands address that has historically outperformed many Sarasota County markets in appreciation and desirability. Offered furnished, including household goods, linens, décor, and months of future bookings in place, this is the type of property capable of generating strong occupancy with minimal downtime while also serving as a long-term appreciation play in one of Florida’s most supply-constrained markets. For lifestyle buyers, the appeal becomes even more personal. Imagine morning walks to coffee on the Circle, afternoons at Lido Beach, sunset dinners without needing a car, and evenings entertaining poolside after a day on the water. Whether used as a seasonal retreat, a lock-and-leave second home, or a full-time residence for a buyer seeking a lower-maintenance alternative to condominium living, this home delivers the rare combination of freedom, convenience, privacy, and coastal charm. In an area where many properties require extensive updating or command significantly higher prices, this home represents a rare opportunity to own a turnkey St. Armands residence with lifestyle appeal, income potential, and long-term investment strength wrapped into one exceptionally charming property.
Listing is courtesy of: EXP REALTY LLC (800-486-1794)
Listing Agent: Carlo Salerno (305-619-1803)
6308 MIDNIGHT PASS RD #6, SARASOTA, FL 34242
$995,000335 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 ArmsSpa: NoVilla
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)
6300 MIDNIGHT PASS RD #21, SARASOTA, FL 34242
$869,000130 Days on yellowkey MLS ID: A4678951
0 Days Off yellowkey (back on 5/26/2026)
REDUCED by $30,000 (3.3%) on 05/26/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1253 Built: 1969 Tax: $5,276 (2025)Community: Crystal Sands 1Villa
Taxes:$5,276
Remarks: Under contract-accepting backup offers. Everything is brand new in this beautifully renovated, turnkey furnished two bedroom, two bath end-unit villa offering an exceptional Siesta Key beach lifestyle just steps from the Gulf. The desirable split floor plan features spacious bedrooms, generous closets, and an open-concept living area filled with natural light, enhanced by a sun-lit Florida room. The updated kitchen is thoughtfully designed with granite countertops, a coordinating backsplash, soft-close cabinetry, and new stainless steel appliances. The primary suite offers a wall-to-wall closet, transom window, and sliding glass doors opening to the Florida room. Additional highlights include luxury vinyl plank flooring, all-new furnishings, and an attached one-car garage with washer and dryer plus ample storage for beach gear. Whether enjoyed as a private coastal retreat or a lock-and-leave rental opportunity, this residence truly offers the best of both worlds. Crystal Sands is a well-managed, financially stable beachfront community that has remained highly desirable since 1969 due to consistent upkeep and thoughtful renovations. The condominium comprises a collection of one, two, and three bedroom villas along with a Gulf-front high-rise tower, all set within beautifully maintained grounds. Residents and guests enjoy private beach access with umbrellas and loungers, two heated swimming pools, a clubhouse, on-site rental management, and night security, all just moments from Siesta Key’s renowned dining and shopping.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-907-2000)
Listing Agent: Bev Murray (941-724-4995)
7366 POINT OF ROCKS RD, SARASOTA, FL 34242
$26,000,000146 Days on yellowkey MLS ID: A4673754
Bed: 5 Bath: 6.0 Gar: 6 Liv Area Sq Ft: 10600 Built: 2020 Tax: $115,958 (2025)Community: Siesta KeySpa: YesSingle Family
Taxes:$115,958
Remarks: Rising above an enviable stretch of shoreline, this Gulf-front estate showcases timeless architecture and coastal refinement. Designed by CMSA Architects and completed in 2020, the residence features layered rooflines, sculpted stone staircases, and soaring arched windows across more than 180 feet of Gulf frontage. With 10,600 square feet of interiors and 20,982 square feet in total, the home offers a grand yet effortless indoor–outdoor lifestyle, ideal for both elevated entertaining and daily living. A sweeping motor court, mature palms, and a grand double staircase create an immediate sense of arrival. Inside, natural light and uninterrupted Gulf vistas establish a feeling of calm, scale, and sophistication from sunrise to sunset. The great room, lined with floor-to-ceiling arched windows and anchored by a carved-stone fireplace, delivers both serenity and architectural presence. The main kitchen is a triumph of craftsmanship - featuring custom Campbell cabinetry, quartz countertops, designer lighting, Sub-Zero refrigeration, a Wolf six-burner dual-oven range, and a substantial island that anchors the open flow into the living and dining spaces. A prep kitchen and workspace elevate functionality with premium appliances, expansive storage, quartz counters, and a dedicated gift-wrapping wall. The bar and wine room create a refined entertaining destination, defined by custom cabinetry and designer lighting. An iron-and-glass–enclosed, temperature-controlled wine room serves as the focal point, complemented by adjacent illuminated display shelving. Sub-Zero refrigeration, an ice maker, and a Fisher & Paykel dishwasher drawer complete the space. Outdoors, the estate unfolds across three dramatic tiers of Gulf-facing living, featuring arched loggias and a resort-style alfresco kitchen with a wraparound bar that opens seamlessly to the main living spaces. An elevated infinity-edge pool and spa appear to merge with the Gulf, while thoughtfully designed outdoor areas transition effortlessly to a manicured lawn and direct access to the crystal-clear waters at Point of Rocks—where snorkeling, dolphin sightings, and sunset walks become part of daily life. The primary suite forms a private wing, introduced by an illuminated groin-vault corridor that enhances the home’s architectural rhythm. Gulf views fill the bedroom and its terrace, while the bath offers a symmetrically designed retreat with dual vanities, full-height mirrors, multiple chandeliers, a massive double-entry shower, a stone-surround soaking tub, a Sub-Zero–equipped coffee bar, and two exceptional custom closets. Nearby, the office provides a quiet, light-filled workspace. The upper level is devoted to comfort and privacy, offering four well-appointed guest suites, a spacious family room with a wet bar, multiple terraces capturing Gulf views, an additional office, and a laundry room. The ground level is enhanced by indoor–outdoor walkways connecting multiple spaces and generous storage, reinforcing the effortless, resort-style livability. A generator, 3-stop elevator, 6-plus humidity-controlled garage spaces, floor-to-ceiling shades, linear vents, whole-house automation, and shellstone and French oak flooring complete the offering. A short, shaded, tree-lined walk places you at Siesta Key Beach, the No. 1 beach in America by TripAdvisor, offering effortless access to one of the world’s most iconic shorelines.
Listing Agent: Joel Schemmel (941-587-4894)
1800 WEBBER ST, SARASOTA, FL 34239
$4,790,00022 Days on yellowkey MLS ID: A4693157
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3262 Built: 2025 Tax: $12,950 (2025)Community: Poinsettia Park 2Spa: YesSingle Family
Taxes:$12,950
Remarks: Nestled in the heart of West of the Trail, this luxury single-story estate represents the pinnacle of modern living. Encompassing 3,262 square feet, the home features 4 bedrooms, 4 full bathrooms, and 2 half baths, all thoughtfully designed for both comfort and functionality. Set on an expansive 15,930-square-foot lot, the residence offers tranquility just moments from the shops and dining of Southside Village. Enjoy the convenience of a circular driveway with a custom paver design and garage space for three cars. With striking architecture, impeccable craftsmanship, and beautiful, thoughtfully curated finishings—showcasing detailed trim work and refined design throughout—this residence delivers sophistication and all-inclusive resort-style living in one of the area’s most desirable locations. Inside, soaring 18-foot vaulted ceilings and custom tray ceilings enhance the open-concept layout, while 12-foot full pocket sliders seamlessly connect indoor and outdoor living spaces. The living room is anchored by a sleek fireplace, creating a warm yet modern focal point. The chef’s kitchen is equipped with professional-grade gas appliances, a waterfall-edge quartz island, custom cabinetry, and an expansive butler’s pantry for effortless entertaining. A glass-enclosed wine display and tray ceiling details add dramatic appeal. The primary suite features 14-foot ceilings and a spa-inspired bath with a freestanding soaking tub, dual vanities, and a luxurious walk-in shower. All bedrooms include custom California Closets. A designated large office, spacious laundry room, and private gym complete the interior amenities. The home also has a full security system installed. Outdoors, the resort-style backyard showcases a heated saltwater pool and hot tub spa with elegant water features. The back patio, finished with a Brazilian hardwood ceiling, is enhanced with remote-controlled mosquito blinds with sun protection for year-round comfort, as well as a full sound system that can be app controlled. A fully equipped outdoor kitchen, fire pit, and outdoor SunBrite TV create the ultimate entertaining space, while a private putt-putt golf course adds a one-of-a-kind touch to this exceptional property. Please let us know how we can help and give us a call to set up a tour of this beautiful home. Thank you.
Listing is courtesy of: THE STUTZMAN REALTY GROUP, LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
4372 TRAILS DR #15-1, SARASOTA, FL 34232
$310,000122 Days on yellowkey MLS ID: A4678938
REDUCED by $15,000 (4.6%) on 04/30/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1239 Built: 1984 Tax: $2,979 (2025)Community: Lakes Of Sarasota IiCondo
Taxes:$2,979
Elementary School: Brentwood Elementary
Remarks: The sought-after Lakes Estates of Sarasota is a hidden gem offering a wonderful blend of space, privacy, and serene natural beauty. This LAKEFRONT , maintenance-free villa features 2 bedrooms, 2 bathrooms, and over 1,200 square feet of living space. Remodeled in 2020 this split floor plan is enhanced by vaulted ceilings that create an open, airy feel. The eat-in kitchen is thoughtfully designed for both everyday living and entertaining, featuring a charming plant window, breakfast bar, and seamless connection to the dining and living areas. Just off the living room, a generously sized screened-in porch provides the perfect setting for indoor-outdoor living and entertaining, with peaceful lake views just beyond. The primary suite serves as a private retreat, complete with a walk-in closet and an en-suite bath with a stand-up shower. French doors open directly to a covered screened deck, placing you just steps from the water and offering a remarkable start or end to each day. NEW HVAC 8/2025 and adding to the property’s comfort and convenience is a one-car garage plus a carport. Residents enjoy winding, tree-lined, lighted streets and a scenic waterfront walking path that leads to the community’s resort-style amenities, including two pools, tennis and pickleball courts, fitness center, clubhouse, playground, and a picturesque central lake with fountain for added ambiance. Just a few blocks away, the pristine Legacy Trail offers 18 miles of paved paths stretching from Sarasota to Venice, perfect for biking, walking, and outdoor exercise, with relief pavilions and eateries along the way. The location is exceptional—minutes from area beaches, shopping, dining, and entertainment. Located in a popular school district, Lakes of Sarasota is not an age-restricted community, making this villa ideal for a wide range of lifestyles for those seeking a balance between suburban tranquility and easy access to urban amenities.
Listing is courtesy of: GRECO REAL ESTATE (941-685-0449)
Listing Agent: Karen Greco (941-504-6927)
4732 MEADOWVIEW CIR, SARASOTA, FL 34233
$564,90015 Days on yellowkey MLS ID: A4693999
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2148 Built: 1987Monthly Fee: $67 Tax: $5,347 (2025)Community: SouthfieldSpa: NoSingle Family
Taxes:$5,347
Remarks: Nestled within the desirable Southfield community, this beautifully designed lakefront residence offers the perfect blend of comfort, elegance, and everyday Florida living. Featuring three bedrooms and two full baths, the home is thoughtfully designed with spacious formal living and dining rooms, along with an inviting family room highlighted by a charming fireplace and soaring volume ceilings. Designed for both entertaining and everyday living, the gourmet kitchen is beautifully appointed with stainless steel appliances, abundant cabinetry, and a built-in desk area ideal for organization or working from home. Most rooms throughout the home offer direct access to the expansive covered lanai, creating a seamless connection between indoor and outdoor living spaces. The spacious guest bedrooms provide comfort and privacy for family and visitors alike, while the luxurious primary suite serves as a true retreat featuring a very large walk-in closet, an oversized Roman shower, and a relaxing soaking tub. Step outside to your private backyard oasis where a heated kidney-shaped pool is enclosed within a large, screened pool cage overlooking tranquil lake views and lush mature landscaping. The fenced yard offers plenty of space for pets and outdoor enjoyment, while the serene setting provides both privacy and beauty. Completing the home is a spacious two-car garage and a prime location within one of Sarasota’s established communities, convenient to shopping, dining, golf, and Gulf Coast beaches.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Stephanie Church (941-724-5448)
5400 OCEAN BLVD #6-4, SARASOTA, FL 34242
$1,250,000273 Days on yellowkey MLS ID: A4663880
REDUCED by $50,000 (3.8%) on 04/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1187 Built: 1970 Tax: $10,071 (2025)Community: TerraceCondo
Taxes:$10,071
Remarks: One or more photo(s) has been virtually staged. MAJOR PRICE REDUCTION! The lowest-priced 2-bedroom residence at Beach Terrace in over 8 years—this is the opportunity of the decade! Welcome to one of Siesta Key's most desirable addresses. This exceptional corner residence offers direct Gulf of Mexico frontage, perfectly positioned at the end of the village where luxury meets convenience. Prepare to be captivated by panoramic vistas from your three spacious private balconies. Enjoy unobstructed views of pristine white sand beaches, sparkling aqua Gulf waters, downtown Sarasota's skyline, and even Longboat Key on clear days. Watch the twinkling lights of Siesta Key Village create an unforgettable backdrop as the sun sets—easily among the best views on Siesta Key. Enter through an inviting foyer with elegant tiled flooring leading into a beautifully updated kitchen featuring granite countertops, modern cabinetry, and stainless appliances. The spacious living area showcases dual sliding glass doors framing stunning Gulf views. The generous dining area provides ample space for entertaining. The primary bedroom features a private Gulf-view balcony with two full-size beds and an elegant ensuite bath with updated tile, modern cabinetry, and granite countertops. The guest bedroom offers a full bed and private sliding door to dazzling Gulf views, plus an updated full bathroom with modern finishes and tile shower. Elevated heated saltwater pool with sunset views, modern fitness center, community room, covered parking, and gated security with onsite management. Private beach access puts you steps from world-renowned Siesta Key Beach. Nestled at the end of the village, enjoy tranquility and convenient access to Siesta Key Village shops and restaurants—no car needed once you arrive. Beach Terrace represents the pinnacle of Gulf-front living. With the lowest pricing for a 2-bedroom in over 8 years, this move-in ready split-floor plan residence is your once-in-a-decade opportunity to own paradise where stunning views, luxury amenities, and coastal elegance unite.
Listing Agent: Mickey Kiernan (941-402-9115)
105 TUCKER AVE, SARASOTA, FL 34232
$599,995126 Days on yellowkey MLS ID: A4680183
REDUCED by $25,005 (4.0%) on 05/26/2026
Bed: 3 Bath: 1.5 Gar: 2 Liv Area Sq Ft: 1562 Built: 1940 Tax: $4,798 (2025)Community: Tuckers SubSpa: YesSingle Family
Taxes:$4,798
Elementary School: Fruitville Elementary
Remarks: A rare opportunity to acquire a beautifully restored 1940 coastal-inspired Key West style Florida bungalow positioned on an oversized 0.38-acre parcel offering future subdivision potential. Following closing, the property may be split into three separate lots, creating one residence lot with the existing home, and two additional buildable parcels—an exceptional value-add opportunity in a highly desirable Sarasota location. The 3-bedroom, 1.5-bath residence blends architectural character with curated modern upgrades. Interior highlights include refinished bamboo and wood flooring, exposed wood ceiling beams, and custom cedar built-ins that enhance the home’s refined coastal Key West bungalow aesthetic. The chef’s kitchen is thoughtfully designed with solid wood cabinetry, quartz countertops, an imported Italian tile backsplash, and updated stainless steel appliances. An adjacent addition provides expanded pantry storage and a laundry area, leading to a spa-inspired primary bathroom featuring dual vanities, a freestanding soaking tub, and a walk-in rain shower. The upper level hosts a private primary suite with a generous walk-in closet with built-ins, a second bedroom, and an updated half bath, while the third bedroom is conveniently located on the main level—ideal for guest accommodations or flexible use. Outdoor living has been elevated to an almost resort-style experience, featuring a 12-foot above-ground pool/spa with custom wood decking, multiple patios finished with imported Italian crystal tile, and a lush botanical setting with over 200 plantings and mature fruit trees including banana, mango, avocado, peach, and guava. Additional amenities include a pavilion, private outdoor shower, and a firepit designed for elevated entertaining and relaxation. Significant capital improvements include a 2023 metal roof, hurricane-rated windows, 2021 HVAC system, 2022 water heater, recent connection to public water, and a 2024 well pump with filtration system also on property. The home offers insulated and drywalled interiors, newly installed wheelchair-accessible outdoor walkway paths, an extended 6+ vehicle driveway, and a 12x14 detached workshop or garage, further enhancing functional versatility. With no HOA, no deed restrictions, and no flood insurance required, this property presents an exceptional combination of lifestyle appeal and long-term investment flexibility. Ideally located just minutes from downtown Sarasota’s premier dining, shopping, and cultural attractions, this offering is well-suited for private ownership, redevelopment, or strategic portfolio expansion.
Listing is courtesy of: DREAMIFY REAL ESTATE LLC (941-827-0700)
Listing Agent: Michael Grant (941-800-8585)
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