Location: Sarasota
Do Not Show Listings
156 SIESTA DR, SARASOTA, FL 34242
$1,649,000320 Days on yellowkey MLS ID: A4661717
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2901 Built: 1977 Tax: $19,016 (2024)Community: Siesta Rev ResubSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$19,016
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Situated in the sought-after Bay Isle community on Siesta Key, this exceptional three-level pool home combines the best of upscale coastal living with impressive rental performance. Designed to host gatherings of all sizes, it is perfectly suited as a primary residence, vacation escape, or income-producing property. In 2024, it brought in $132,419 in gross rental income, with 2025 projections at $120,681, showcasing its strong investment appeal. Just a short stroll to Shell Beach and minutes from Siesta Key Village and the world-renowned Siesta Key Beach, the home offers unmatched access to award-winning white sand, vibrant dining, and boutique shopping. A complete renovation in 2019 transformed the property with a new metal roof, hurricane-impact windows, patio and garage doors, upgraded AC systems, and an oversized resurfaced lap pool with all-new equipment, including a heat pump. Over 50 Areca palms frame the lush tropical landscaping, providing beauty and privacy while remaining easy to maintain. The outdoor living space rivals a private resort, featuring a sparkling pool, spacious patio, and tranquil surroundings ideal for lounging or entertaining. Inside, natural light fills the open floor plan, creating seamless flow to the outdoor areas and making it a true entertainer’s haven. Impeccably maintained and move-in ready, this Bay Isle residence offers a rare opportunity to enjoy the island lifestyle while benefiting from consistent rental income.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Curt Ware (941-587-9122)
5908 BRIAR ROSE WAY, SARASOTA, FL 34232
$435,00041 Days on yellowkey MLS ID: A4693050
REDUCED by $33,900 (7.2%) on 05/31/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1494 Built: 2019Monthly Fee: $81 Tax: $2,999 (2025)Community: Garden Village Ph 1Single Family
Taxes:$2,999
Elementary School: Fruitville Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: McIntosh Middle
Remarks: Welcome home! This beautifully updated 3-bedroom, 2-bath home with a 2-car garage checks all the boxes. It is located in one of the most affordable gated communities in the area. The main living area flows effortlessly from room to room, perfect for everyday living and entertaining. You will find thoughtful upgrades throughout including crown moulding in the common areas, electrical upgrades and fresh interior paint. The kitchen has been upgraded for you with granite countertops, all appliances and even a new kitchen sink. Step into the master suite with an ensuite bathroom with granite countertops, upgraded toilet and new shower enclosure. The guest bathroom also features the same granite countertops, upgraded toilet and new shower enclosure as well. Comfort is covered with a whole-home water softener, carpet lain over tile, that could easily be removed, for cozy underfoot warmth. Continue through the home and step outside to your private backyard retreat featuring stunning paver and stonework — low maintenance with a drip irrigation system in the backyard keeping things lush without the work yet designed to impress. Located 2 mins away from I75 for easy commuting and 15 min to Siesta Key Beaches and 10 min from downtown, so conveniently located to everything! This home is truly a move-in ready gem. Come see it before it's gone!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Gary Turner (941-914-2500)
9085 LUNA LN, SARASOTA, FL 34241
$940,00053 Days on yellowkey MLS ID: A4691879
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3334 Built: 2021Monthly Fee: $251 Tax: $9,809 (2025)Community: Cassia At Skye RanchSpa: NoSingle Family
Taxes:$9,809
Elementary School: K-8 At Clark And Lorriane
High School: Riverview High
Middle School: K-8 At Clark And Lorriane
Remarks: Magazine-Worthy Luxury Meets Resort Living in Skye Ranch! This sought after Barbados Model offers an impressive 4,347 total area sq ft, showcasing refined finishes, extensive upgrades, and exceptional attention to detail throughout. At the heart of the home, the entertaining chef's kitchen is a true showpiece, appointed with an expanded generous quartz-topped island with touchless faucet, insta hot and insta cold filtered water, double pantry and a spacious dining area with bay windows overlooking the beautiful outdoor landscape. The open main level also offers 2 dedicated living rooms, providing flexibility for work, relaxation, or recreation. A homeowner's everyday living delight with a dedicated drop zone off the garage and front entrance, designed for a central area of organization. The main living areas are enhanced by soaring ceilings, 8 foot interior doors and expansive open spaces designed for both everyday comfort and effortless entertaining. Upstairs is ideal for guests or multigenerational living. Meticulously maintained and beautifully appointed, this 4 bedroom residence features 3 full bathrooms and 1 half bath. The spacious primary suite serves as a private retreat, offering direct access to a private screened balcony, along with two custom walk-in closets and a spa-inspired bathroom. The second level also includes one other private ensuite bedroom and bathroom and additionally two bedrooms linked with a shared bathroom. Lastly a spacious bonus room with almost 250 square feet of versatile space allows it to be tailored to your lifestyle with effortless flow. Outdoor living is truly resort-inspired. The screened in lanai is a graciously sized area overlooking the beautifully landscaped yard. Additional highlights include a large laundry room and 3 car air conditioned garage offering ample storage or a car enthusiast dream. Halo REMI air purification system on dual-zone air conditioning units. Both the interior and exterior have been newly painted, enhancing the home’s fresh move-in-ready appeal. The home is ideally situated on a wide, well-planned street with generous shoulder space, offering convenient parking for residents and guests. Perfectly positioned alongside a scenic nature trail, the home provides direct access to the community’s main entertainment and amenity areas, seamlessly blending tranquility with an active lifestyle. Indulge in luxury living at its finest within the Cassia at Skye Ranch community. Residents enjoy privileged access to The HUB, an extraordinary 25,000+ square-foot amenity center designed to rival a private resort. This features a state-of-the-art fitness center, movement studios, game room, indoor basketball and pickleball courts, rock-climbing wall and a stylish café creating an elevated daily experience just moments from home. Outdoors, a collection of resort-style pools, a junior Olympic lap pool, splash zone, and beautiful gathering spaces invite relaxation and recreation year-round. The community further offers scenic nature trails, playgrounds, outdoor sports courts and a calendar of social events, fostering a true sense of connection and belonging. Skye Ranch provides quick access to I-75, along w/ Sarasota’s premier Beaches, Myakka Park, shopping, dining and cultural destinations. Located in one of the best school districts in the state and direct access to the new K-8 Skye Ranch School. LOW CDD. Don’t miss the opportunity to experience this exceptional lifestyle.
Listing Agent: Chelsie Mocoroa Gobel (425-343-2437)
7125 WESTMORELAND DR, SARASOTA, FL 34243
$3,595,000193 Days on yellowkey MLS ID: A4675672
REDUCED by $30,000 (0.8%) on 05/06/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4343 Built: 2025 Tax: $4,490 (2024)Community: North IslesSingle Family
Taxes:$4,490
Elementary School: Bayshore Elementary
High School: Bayshore High
Middle School: Electa Arcotte Lee Magnet
Remarks: One or more photo(s) has been virtually staged. The Abaco Model is a stunning Sarasota luxury residence offering 4,343 square feet of refined living space and 6,273 square feet under roof, featuring four true bedrooms and six total rooms. This home is Florida Green Home Bronze Certified, reflecting thoughtful construction, energy efficiency, and sustainable building practices. Upon arrival through dramatic 10-foot iron front doors, the foyer provides a breathtaking sightline through the home to the pool and canal beyond. The oversized great room is ideal for entertaining and showcases stained cypress beams, a gas fireplace with full-height tile surround, and a 16-foot-wide by 10-foot-high pocketing sliding glass door that opens seamlessly to the outdoor living and pool area. The chef’s kitchen features an oversized island with gas cooktop, walk-in pantry, and sunlit windows above the sink for abundant natural light. The private owner’s wing includes a refined library or office adjacent to the owner’s suite, both enjoying water views. Dual oversized customized built in walk-in closets and a spa-inspired owner’s bath complete the retreat with a freestanding soaking tub, walk-in shower, private water closet, and separate his-and-her vanities. Two additional guest suites accommodate king-sized beds and feature ensuite baths and walk-in closets. A waterfront bonus room at the rear of the home also enjoys water views and is serviced by a nearby full bath that also functions as a powder bath and pool bath. Two additional flexible sleeping rooms bring the total sleeping capacity to six. The expansive outdoor living and dining area overlooks the pool and spa and includes a cozy gas fireplace, creating the perfect waterfront entertaining setting. The three-car garage leads into a walk-in laundry room with a dedicated storage closet. All windows and exterior doors feature Low-E impact glass, all interior doors are 8-foot shaker style, all interior walls include sound batt insulation, walls and ceilings have smooth finishes, and all interior floors are tiled throughout. Cabinetry is by Wood-Mode/Brookhaven. The West Indies–inspired exterior elevation features shutters, corbels, decorative brackets, and a concrete tile roof. The private dock includes a high-capacity 33,000-pound boat lift with water and power and is capable of accommodating 40–50-foot vessels with protected deep-water access and quick entry to Sarasota Bay making this property ideal for the serious boater.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Lauren Holt, Pllc (941-928-7211)
5252 LAKE VILLAGE DR ## 54, SARASOTA, FL 34235
$249,00071 Days on yellowkey MLS ID: A4690508
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1065 Built: 1983 Tax: $2,454 (2025)Community: Village LakeCondo
Taxes:$2,454
Remarks: Rare tree-house feel from the lanai overlooking a lush nature trail distinguishes this upgraded, turnkey residence in The Meadows—offering refined, maintenance-free living just steps from resort-style amenities. A true move-in-ready opportunity, enhanced by a 2023 HVAC system, 2025 kitchen and bath updates, and tasteful furnishings included, delivering effortless Florida luxury in a serene, pet-friendly setting. A private lanai frames tranquil, preserved natural views, complemented by nearby access to a heated community pool & gas BBQ grilling area, ideal for relaxed outdoor living. Thoughtfully updated, the residence features new carpeting (2024) and a new HVAC system (April 2023) with annual maintenance. The kitchen is appointed with dolomite and marble countertops, new appliances—including refrigerator, stove, dishwasher, sink, and faucet—and upgraded fixtures and hardware, along with refined lighting enhancements (2023, 2026). The desirable split-bedroom layout ensures privacy for owners and guests, with each bedroom offering its own ensuite bath. The primary suite enjoys serene treetop views, dual closets, and a vanity with tub/shower combination, while the guest suite provides a private full bath. Offered fully furnished(in 2021), this residence is completely turnkey and includes linens, cookware, dishes, TV, and essential household items. Additional conveniences include in-unit laundry with stacked washer and dryer, assigned parking, and guest parking. Ideally located within walking distance to Meadows Village Shops, residents enjoy immediate access to dining, wellness services, medical offices, and the seasonal Farmers Market. The Meadows community is renowned for its extensive trail system, scenic lakes, fitness center, pickleball courts, pool and spa, dog park, and vibrant calendar of social activities—all within a secure, 24-hour gated environment. Optional tennis and golf memberships further enhance the lifestyle offering. Not located in a flood zone and offering small dog approval (per association guidelines), this residence presents an exceptional opportunity to experience elevated, turnkey living in one of the area’s most desirable communities. A secure storage facility for boats, RVs, and trailers is also available within The Meadows.
Listing is courtesy of: ALBERT WOOSTER & COMPANY (941-350-1220)
Listing Agent: Kathleen Niedospial (941-780-2884)
5519 PALM AIRE DR, SARASOTA, FL 34243
$344,90099 Days on yellowkey MLS ID: A4686305
0 Days Off yellowkey (back on 5/31/2026)
REDUCED by $5,000 (1.4%) on 05/18/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1632 Built: 1977 Tax: $4,154 (2025)Community: Palm-Aire At Sarasota 7-CVilla
Taxes:$4,154
Remarks: Under contract-accepting backup offers. Beautifully updated Palm Aire villa with expansive GOLF COURSE AND POND VIEWS, offering exceptional privacy and serene natural surroundings. This TURNKEY FURNISHED home is move-in ready, perfect for full-time or seasonal living. Thoughtfully upgraded throughout, the villa features luxury vinyl plank flooring in the main living areas, creating a bright, open feel. The updated kitchen includes wood cabinetry, quartz countertops, pantry, stainless steel appliances, breakfast bar, and a spacious dining area. The primary suite offers a walk-in closet and updated en-suite bath with quartz countertops, modern cabinetry, and walk-in shower. The guest bedroom provides comfortable accommodations, and the second bath features updated finishes and a tub/shower combination. A remodeled Florida Room with hurricane impact windows serves as an ideal bonus space for dining, relaxing, card playing or entertaining while enjoying tranquil lake and nature views. Additional highlights include a GARAGE, fresh interior paint, new window treatments, and updated ceiling fans. The interior furnishings are high quality and will not disappoint! Enjoy carefree living as the roof, exterior building and ground maintenance are handled by the association. Conveniently located near shopping, dining, entertainment, and world-renowned beaches. Enjoy easy access to Conservatory Park and a community pool just a short walk away. Optional membership to Palm Aire Country Club offers golf, tennis, pickleball, fitness, and dining. Schedule your private showing today—this one won’t last! I
Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE (941-556-9100)
Listing Agent: Jan Jordan (941-737-4169)
1350 MAIN ST #712, SARASOTA, FL 34236
$589,000151 Days on yellowkey MLS ID: A4680431
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 944 Built: 2007 Tax: $6,909 (2024)Community: 1350 Main ResidentialSpa: YesCondo
Taxes:$6,909
Remarks: Experience the best of downtown Sarasota living in this light-filled residence, ideally positioned in the heart of the city with an exceptional walkable lifestyle. Restaurants, coffee shops, galleries, the marina, and Sarasota Bay are just steps from your door, placing you at the center of Sarasota’s vibrant cultural and culinary scene. Located on the desirable bayfront-facing side of the building, the residence enjoys open views along Palm Avenue and abundant natural light through expansive windows and sliding glass doors. The private balcony offers the perfect vantage point for morning coffee or evening relaxation while overlooking the energy of downtown. Inside, high ceilings and an open-concept layout create an inviting sense of space. Tile flooring flows throughout the main living areas, connecting seamlessly to the European-style kitchen. Designed for both everyday living and entertaining, the kitchen features streamlined cabinetry, generous counter space, stainless steel appliances, and a serving bar that opens to the living area. The oversized bedroom serves as a peaceful retreat, complete with a spacious walk-in closet and a well-appointed en-suite bath featuring dual vanities, a soaking tub, and a frameless glass shower. A separate powder room, ample storage, and a building-wide water softener and filtration system add everyday comfort and convenience. This pet-friendly residence includes one assigned parking space and a climate-controlled storage unit. Residents enjoy access to a full suite of amenities, including 24-hour concierge service, a state-of-the-art fitness center with steam rooms, a 72-foot heated lap pool and spa, media and social rooms, a library, and a guest suite for visiting friends and family (available on a first-come basis). Step outside and enjoy Sarasota’s renowned lifestyle offerings—walk to the farmers market, dine along Palm Avenue, attend performances at the Sarasota Opera House or Van Wezel Performing Arts Hall, or head over the bridge to Lido Key Beach and St. Armands Circle. Whether as a full-time residence or seasonal retreat, this downtown Sarasota property delivers modern comfort, resort-style amenities, and unmatched proximity to everything that defines city living on Florida’s Cultural Coast.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
1125 LONGFELLOW WAY #125-B, SARASOTA, FL 34243
$155,00061 Days on yellowkey MLS ID: A4691728
REDUCED by $10,000 (6.1%) on 05/31/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1365 Built: 1979Monthly Fee: $631 Tax: $2,421 (2025)Community: Shadybrook Village AmdCondo
Taxes:$2,421
Remarks: If you’re searching for a Sarasota townhome that offers low-maintenance living, peaceful preserve views, and a central location, this upgraded end-unit is a standout. Move-in ready and thoughtfully updated, the home features an open-concept layout with 3 bedrooms and 2.5 baths designed for comfortable everyday living. As an end unit, it enjoys additional natural light and enhanced privacy features that set it apart within the community. Step outside to your private patio overlooking a tranquil preserve, creating a quiet outdoor retreat. Inside, the home has been refreshed with quartz countertops, updated cabinetry, modern lighting and plumbing fixtures, fresh interior paint, and new carpet throughout. The washer and dryer are included, making this a true turnkey opportunity. The community has also recently completed new roofs, adding to the home’s overall value and peace of mind. Location is one of the property’s strongest assets. Just minutes from University Parkway, UTC Mall, dining, golf, SRQ Airport, downtown Sarasota, and the Gulf beaches, it offers exceptional convenience for both full-time and seasonal residents. Community amenities include a swimming pool, tennis courts, basketball court, and clubhouse, supporting an active Florida lifestyle without the upkeep of a single-family home.
Listing is courtesy of: SARABAY REAL ESTATE INC (941-355-7696)
Listing Agent: Jessie Bonner (941-356-3182)
7254 KODIAK LN, SARASOTA, FL 34240
$679,000105 Days on yellowkey MLS ID: TB8486718
1 Days Off yellowkey (back on 5/31/2026)
REDUCED by $5,000 (0.7%) on 05/17/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2218 Built: 2025Monthly Fee: $375 Tax: $3,651 (2025)Community: Emerald Lndg/WatersideSingle Family
Taxes:$3,651
Elementary School: Tatum Ridge Elementary
High School: Booker High
Remarks: Offered partially furnished, this Waterside home presents a rare opportunity to step into the Florida lifestyle with ease and comfort. Located in the heart of the vibrant Waterside district of Lakewood Ranch, this stunning home in Emerald Landing is the perfect blend of luxury living and unbeatable access to everything happening nearby. Just moments from the shops, restaurants, events, and waterfront atmosphere of Waterside Place, this home is ideal for buyers who want to enjoy a walkable lifestyle while still retreating to a beautifully designed private residence. This popular ‘Bullhead’ floor plan offers 3 bedrooms, 2.5 bathrooms, a dedicated study, and an expansive upstairs loft across more than 2,200 square feet of thoughtfully designed living space. The soaring 12-foot ceilings in the main living area create an open, airy feel filled with natural light. Just off the entry, a private study with French doors provides the perfect home office or library. At the center of the home, the designer kitchen shines with a gas cooktop, under-cabinet hood, built-in microwave and oven, and an open layout that flows seamlessly into the living and dining spaces—ideal for both entertaining and everyday living. The first-floor Owner’s Retreat offers a peaceful escape with a spa-like bathroom featuring a freestanding soaking tub and a custom-organized walk-in closet. Upstairs, two additional bedrooms share a full bath alongside a spacious loft that works beautifully as a second living area, workspace, or flexible bonus room. Outdoor living is just as inviting with a charming front porch and a rear paver patio perfect for relaxing or entertaining. A rear-loading oversized two-car garage includes epoxy flooring, built-in cabinetry, overhead storage racks, and ample organization. Throughout the home, thoughtful upgrades elevate the space, including designer lighting, plantation shutters, custom closet and pantry systems, and impact glass for added peace of mind. Residents of Emerald Landing enjoy exclusive community amenities, including a resort-style pool, clubhouse, pickleball courts, dog park, and a unique water taxi that departs from the community dock to Waterside Place—home to the renowned Waterside Place Farmers Market every Sunday. If you’re looking for a home that offers luxury finishes, low-maintenance living, and the ability to walk, bike, or boat to the best dining, shopping, and events in Waterside, this one is a must-see. Schedule your private showing today.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Michael Chenkus (941-363-1883)
5830 MIDNIGHT PASS RD #48, SARASOTA, FL 34242
$558,00030 Days on yellowkey MLS ID: A4695273
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 728 Built: 1963 Tax: $3,659 (2025)Community: Jamaica RoyaleCondo
Taxes:$3,659
Remarks: Welcome to your own slice of paradise at Jamaica Royale, located directly on the world-famous shores of Siesta Key Beach. This beautifully remodeled one-bedroom, one-bath condominium, complete with a queen sleeper sofa, and a twin sleeper sofa, offers the perfect combination of coastal sophistication and exceptional rental income potential. Thoughtfully updated throughout, the stunning kitchen features elegant quartz countertops, custom wood cabinetry, stainless steel appliances, and a convenient laundry closet with a stackable washer and dryer—ideal for effortless beachside living and entertaining. The spa-inspired bathroom showcases designer finishes, including a custom-tiled shower and sleek quartz top vanity. Designed with both comfort and style in mind, the open and inviting floor plan is offered fully furnished and turnkey, allowing you to begin enjoying the Siesta Key lifestyle immediately. Whether you're seeking a personal beachfront getaway, an investment property, or both, this residence delivers. Jamaica Royale is one of Siesta Key's most sought-after beachfront communities, offering flexible one-week minimum rentals, making it highly attractive to vacationers and investors alike. Residents and guests enjoy 3 heated community pools, designated BBQ areas, a shuffleboard court and approximately 300 feet of private beachfront, with direct access to the Gulf of Mexico's crystal-clear waters and powder-soft quartz sand. Perfectly positioned just minutes from Siesta Key Village, you'll enjoy easy access to award-winning restaurants, charming boutiques, entertainment, and vibrant nightlife. This is a rare opportunity to own a turnkey beachfront retreat in one of Florida's most desirable coastal destinations—where every day feels like a vacation.
Listing is courtesy of: PEPPERTREE BAY REALTY INC (941-914-3380)
Listing Agent: Eliza Miller (941-914-3380)
6140 MIDNIGHT PASS RD #902, SARASOTA, FL 34242
$925,000270 Days on yellowkey MLS ID: A4666851
REDUCED by $20,000 (2.1%) on 04/12/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 1000 Built: 1967 Tax: $10,547 (2025)Community: Horizons WestCondo
Taxes:$10,547
Elementary School: Gulf Gate Elementary
Middle School: Brookside Middle
Remarks: Your Dream Beach Escape Awaits on Siesta Key! Tired of long winters or hectic city life? Discover the ultimate retreat in this luxurious 9th-floor penthouse overlooking Siesta Key’s world-renowned Crescent Beach. With uninterrupted Gulf views, you’ll enjoy breathtaking sunsets and the soothing sounds of the surf each day. This spacious 1-bedroom, 1-bath unit features a sleek open floorplan with panoramic views from the living, dining, and kitchen areas. Fully furnished and move-in ready, it includes impact windows and doors, 2021 AC, new glass railings for unobstructed beach views, and updated appliances. The bedroom offers custom closets and en-suite bath with a modern walk-in shower. A large walk-in pantry provides extra storage. Add a sleeper sofa or Murphy bed to easily host guests. Located in Horizons West, a 7-acre gulf-to-bay community with 300 feet of private beach, beachside pool and spa, grilling areas, clubhouse, and a bayside park with day dock—perfect for kayaking, fishing, or relaxing by the intracoastal waterway. A second pool is located next to the Community Clubhouse. Hop on the free Siesta Key trolley to explore local dining, shopping, and entertainment. This is more than a condo—it’s your gateway to paradise.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Suki Scollo (941-587-2289)
2315 RIVERWOOD PINES DR, SARASOTA, FL 34231
$595,00031 Days on yellowkey MLS ID: A4695340
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2031 Built: 1973 Tax: $5,385 (2025)Community: Riverwood PinesSpa: NoSingle Family
Taxes:$5,385
Elementary School: Phillippi Shores Elementary
Remarks: Welcome to this beautiful 4-bedroom, 2-bath pool home featuring an open-concept layout and numerous recent updates, including new flooring and a newer roof. This move-in-ready property offers a maintenance-free yard and is situated on a spacious oversized cul-de-sac lot with ample parking space for your cars, boats, toys, and guests. The home also features an oversized 2-car garage, a gorgeous dining area, and is being sold fully furnished, making it ideal as a primary residence, second home, or investment property. Located in a highly desirable school zone, this home is only a 12-minute drive to Siesta Key Beach, close to shopping and dining, and just 4.5 miles from Downtown Sarasota. With no HOA or CDD fees and no rental restrictions, this property offers endless flexibility and an incredible opportunity to enjoy the Florida coastal lifestyle. Bring your toys and start living the Florida dream today!
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Nikola Zafirovski (386-898-4335)
2705 SUNNYSIDE ST, SARASOTA, FL 34239
$599,00031 Days on yellowkey MLS ID: A4695026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1671 Built: 1958 Tax: $5,729 (2025)Community: South GateSingle Family
Taxes:$5,729
Remarks: This beautifully renovated mid-century modern home in the highly sought-after SOUTH GATE neighborhood is the perfect blend of vintage charm and modern luxury. Completely updated from top to bottom, this stunning 3-bedroom, 2-bath residence features brand new flooring throughout, fully remodeled bathrooms, fresh interior and exterior paint, a beautifully redesigned kitchen with all new appliances, and professionally updated landscaping that enhances the home’s curb appeal. Major system upgrades include a metal roof with aluminum super gutters, updated A/C unit, replumbed PVC plumbing, and modernized electrical systems, offering peace of mind for years to come. The flexible floor plan provides the option to easily convert the home into a 4-bedroom layout if desired. Conveniently located with easy access to downtown Sarasota, Siesta Key Beach, Arlington Park, shopping, dining, and entertainment, this home offers the ultimate Florida lifestyle. Whether you’re enjoying a sunset stroll, relaxing at one of the world’s most beautiful beaches, or dining nearby, this location truly has it all. This is the kind of investment and lifestyle opportunity that doesn’t come around often — move-in ready, beautifully updated, and perfectly located. Don’t miss your chance to own a piece of Sarasota paradise!
Listing is courtesy of: MACHADO PROPERTY PROS (941-587-7488)
Listing Agent: Jen Hendrickson (941-726-9985)
1624 STICKNEY POINT RD #101, SARASOTA, FL 34231
$450,00031 Days on yellowkey MLS ID: TB8511188
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1021 Built: 1975Monthly Fee: $992 Tax: $3,669 (2025)Community: Castel Del MareSpa: NoCondo
Taxes:$3,669
Remarks: Fully Remodeled Coastal Retreat – Move-In Ready & Just Steps from the Water! You must see this completely renovated, first-floor condo in beautiful Sarasota—offering effortless coastal living with a partial view of Little Sarasota Bay and just a short walk to the beach! This fully furnished, turn-key unit was completely gutted and redesigned in 2025, featuring high-end finishes and modern upgrades throughout. From the moment you walk in, you’ll notice the attention to detail as everything is brand new! Interior Highlights: Luxury LVP flooring throughout Brand new kitchen cabinets & stone countertops Brand new appliances Stylish modern light fixtures Spacious master bedroom with walk-in closet and door to screened in porch Master bath with stand-up shower & glass surround New vanities and toilets in both bathrooms New water heater Beautiful screened-in patio with new tile flooring Brand new hurricane proof sliding glass door to patio and windows throughout the unit Step outside your door and enjoy the convenience of ground-floor living in building 3, with tennis and pickle-ball courts just steps away. Community Amenities Include: 2 swimming pools Tennis & pickle-ball courts Shuffleboard court Fishing pier/gazebo on the Intracoastal waterway Sidewalks throughout community Clubhouse On-site property management Community laundry facilities Located directly on the Intracoastal Waterway and only a few blocks from the beach, this condo offers the perfect blend of relaxation, recreation, and convenience. Whether you're looking for a primary residence, vacation getaway, or investment opportunity, this one checks all the boxes. Don’t miss your chance to own a brand-new coastal condo in one of Sarasota’s most desirable locations!
Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)
Listing Agent: Stephen Hachey (813-642-6030)
3410 SPANISH OAK TER, SARASOTA, FL 34237
$155,000655 Days on yellowkey MLS ID: A4622186
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1973Monthly Fee: $210 Tax: $1,696 (2023)Community: Oakwood ManorMobile Home
Taxes:$1,696
Tax Year: 2023
Remarks: Welcome to this beautifully maintained two bedroom, two bath sanctuary—perfect for your second home or retirement dreams. Begin your mornings on the spacious enclosed front lanai, savoring your coffee and the serene surroundings. This charming home features an open floor plan with a bright and airy living room, ideal for entertaining guests or unwinding after a day of activities. The modern kitchen boasts ample counter space and a cozy breakfast nook, making meal prep a delight. The master bedroom offers a peaceful retreat with an en-suite bathroom and a walk-in closet, while the second bedroom is perfect for guests or a home office. You’ll appreciate the convenience of plenty of parking under the carport and a full-size laundry in the shed at the back of the carport. Nestled in the vibrant, gated 90-acre Oakwood Manor community—the only land-owned manufactured home community in the City of Sarasota—this home is a treasure trove of amenities designed to enrich your lifestyle. For a reasonable monthly fee of $210, enjoy a large clubhouse with a commercial kitchen, event stage, fitness room, cozy library, and more. Unwind in the heated pool with a handicap ramp, relax in the spacious hot tub, or partake in outdoor activities like bocce ball, ping pong, and picnicking under beautiful oak trees. This age-restricted social haven is conveniently located next to the scenic Legacy Trail and city pickleball courts. Just a short trip from downtown Sarasota, stylish St. Armands Circle, and the world-renowned Siesta Key Beach, this community offers the ultimate in Florida living. Live where others vacation and make every day a delightful adventure! Please note, no pets or motorcycles are allowed. Come embrace the fun, active lifestyle you’ve always dreamed of!
Listing is courtesy of: COLDWELL BANKER REALTY (941-739-6777)
Listing Agent: Toni Westerfield (941-809-7100)
8438 WEBBER RD, SARASOTA, FL 34240
$1,275,00069 Days on yellowkey MLS ID: A4688777
0 Days Off yellowkey (back on 5/30/2026)
REDUCED by $20,000 (1.5%) on 05/13/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4573 Built: 2010Monthly Fee: $133 Tax: $7,765 (2025)Community: Regent LakeSpa: YesSingle Family
Taxes:$7,765
Remarks: Under contract-accepting backup offers. Back on the market - Buyer was unable to secure financing. Room to truly live, relax, and entertain on over an acre in the intimate 13 home community of Regent Lake. This impressive residence offers five spacious bedrooms, four with private en-suite baths, plus a half bath on the main floor. The thoughtfully designed layout also includes a large upstairs bonus room, perfect as a media room, game room, or private retreat for guests. At the center of the home is a generous open-concept living space where the kitchen, breakfast nook, and family room flow seamlessly together. 10’ ceilings on the main level, 9’ ceilings upstairs, and eight-foot doors throughout add to the home’s spacious feel. Designed with both everyday living and entertaining in mind, the kitchen features an oversized center island, separate breakfast bar, stainless steel appliances, granite countertops, dual built-in convection oven and microwave and a cooktop with a custom wood vent hood. Rich 42-inch wood cabinetry with crown molding, decorative backsplash, and solid wood dovetail drawers with soft-close construction has timeless style. The primary suite is a private retreat featuring dual walk-in closets, a garden tub, walk-in tiled shower, double vanities, and upgraded fixtures throughout. Step outside to more than 1,500 square feet of screened outdoor living space designed for year-round enjoyment. The expansive lanai features a heated spa, saltwater pool, and a fully equipped outdoor kitchen, making it ideal for hosting guests or unwinding at the end of the day. Western rear exposure provides stunning sunset views, while the front of the home enjoys soft morning light. From the lanai and main living areas, take in peaceful views of the 25-acre spring-fed lake, stocked with bass and ideal for canoeing, kayaking, or electric boating. Privately tucked away yet conveniently located near I-75, Gulf beaches, restaurants, and shopping, this home offers the perfect balance of peaceful country-style living and everyday convenience.
Listing Agent: Sherry Johnson (941-730-0897)
4429 OAKLEY GREENE #6, SARASOTA, FL 34235
$349,00038 Days on yellowkey MLS ID: A4694535
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1868 Built: 1986 Tax: $2,604 (2025)Community: Oakley Greene - The Highlands - The MeadowsVilla
Taxes:$2,604
Remarks: Serene, easy-living villa with lush views in the prestigious Highlands section of The Meadows, one of Sarasota’s desirable neighborhoods just 15 minutes from downtown. A canopied street, a paver driveway and a charming courtyard welcome you home. Inside, you will love the comfortable floor plan with natural light, oak flooring and tray ceilings in the living areas with walls of sliders showcasing a tropical setting; truly serene. The kitchen features Kona Beige quartz countertops, white appliances and a convenient grilling patio. The spacious primary en suite features dual counter-height vanities, a walk-in shower and an ample closet. All within 100 feet of the heated community pool, near the nature trails and a short ride to all the fun The Meadows has to offer. The Meadows is a sought-after 1,600-acre park-like community just 15 minutes from downtown. Residents enjoy 14 miles of scenic trails and access to a fitness center, a junior Olympic pool, pickleball, golf and Har-Tru tennis. You’ll also be minutes from award-winning beaches, vibrant arts and culture, Whole Foods, Trader Joe’s, Nathan Benderson Park, the Legacy Trail, Mote SEA Aquarium, the future Sarasota Orchestra Music Center and University Town Center’s shopping, dining and entertainment. A fabulous Florida lifestyle awaits! The residence features a 2020 16 SEER air-conditioning system, a 2015 hurricane garage door, a 2004 tile roof, which is the condominium’s responsibility, fully funded reserves, and is above the floodplain in Zone X.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Fernando Viteri, Pa (941-400-7676)
8456 MIDNIGHT PASS RD, SARASOTA, FL 34242
$1,900,00075 Days on yellowkey MLS ID: TB8497342
REDUCED by $300,000 (13.6%) on 05/30/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 966 Built: 1962 Tax: $7,269 (2025)Community: Heron Lagoon Lodge SubSingle Family
Taxes:$7,269
Elementary School: Southside Elementary
Remarks: Rare Opportunity: Last Unrestricted Deed Waterfront Property on Midnight Pass Siesta Key’s Heron Lagoon. Discover one of the most unique waterfront opportunities left on the Turtle Beach end of Siesta Key. This last unrestricted deed property on legendary Midnight Pass sits directly on the serene Heron Lagoon side, offering unparalleled flexibility with no HOA and endless possibilities for your dream coastal retreat. The existing home is a charming 2-bedroom, 1-bathroom Old Florida bungalow (966 sq ft) that has been thoughtfully remodeled while preserving its authentic island character. Oak trees frame the property, and the one story design blends seamlessly with the natural surroundings on this oversized 0.39-acre lot (approximately 47 ft of direct lagoon frontage). Step outside to your private dock complete with shower and electricity — perfect for kayaking, paddle boarding, straight into Heron Lagoon with quick, effortless access to the Gulf of America via Midnight Pass. Enjoy breathtaking west-facing sunsets every evening as the sky paints vibrant colors over the ocean — a year-round spectacle right from your backyard. Whether you envision keeping the classic bungalow, adding a pool, expanding the home, or building new under Siesta Key’s flexible zoning, this rare unrestricted parcel delivers the ultimate blank canvas. Property Highlights: 2 beds | 1 bath | 966 sq ft living area, 0.39-acre lot with direct Heron Lagoon frontage, Private boat dock with shower & electric, No HOA — unrestricted deed, West-facing Gulf sunsets, Remodeled Old Florida charm, Prime southern Siesta Key location on one of Florida’s most coveted barrier islands, and the recently opened Midnight Pass intercoastal passage to the Gulf. Don’t miss your chance to own a true piece of Siesta Key history and lifestyle. This one-of-a-kind waterfront gem will not last.
Listing is courtesy of: HOMECOIN.COM (888-400-2513)
Listing Agent: Jonathan Minerick (888-400-2513)
10863 ECLIPSE ST, SARASOTA, FL 34241
$849,43473 Days on yellowkey MLS ID: A4690449
1 Days Off yellowkey (back on 5/30/2026)
INCREASED by $25,000 (3.0%) on 05/01/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3505 Built: 2026Monthly Fee: $251Community: Cassia At Skye RanchSingle Family
Taxes:$0
Remarks: Under Construction. What's Special: Conservation View | Dedicated Study | Game Room | No Rear Neighbors. New Construction - September Completion! Built by America's Most Trusted Home Builder. Welcome to the Tybee at 10863 Eclipse Street in Cassia at Skye Ranch! The first floor welcomes you with a dedicated study and a versatile flex room, leading into an open concept great room, dining area, and kitchen with a center island that opens to a covered lanai, making it easy to enjoy indoor and outdoor gatherings. Tucked privately at the back of the home, the primary suite features an attached bath with a dual sink vanity, soaking tub, separate shower, and an oversized walk-in closet, while a conveniently located laundry room sits just off the garage entry to simplify daily routines. Upstairs, four secondary bedrooms share two full baths and gather around a spacious game room that adds even more room to relax or play. Skye Ranch sits in a prime Sarasota location at Clark and Lorraine Roads, offering a vibrant setting with access to the Skye Ranch K-8 school. The community preserves natural beauty with grand oaks, palms, wetlands, lakes, and native wildlife. Miles of trails connect you to nature, parks, and exceptional on-site amenities. Additional Highlights Include: gourmet kitchen, tray ceiling package, impact window throughout the home, a soaking tub with a separate shower in the primary bathroom, outdoor kitchen rough-in, and a shower in bathroom 2 upstairs. MLS#A4690449
Listing is courtesy of: TAYLOR MORRISON RLTY OF FLA (866-495-6006)
Listing Agent: Michelle Campbell (866-495-6006)
2747 JEFFERSON CIR, SARASOTA, FL 34239
$850,00052 Days on yellowkey MLS ID: A4692671
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1560 Built: 1961 Tax: $2,392 (2025)Community: South GateSingle Family
Taxes:$2,392
Remarks: Nestled in the highly desirable Southgate neighborhood, this charming 2 bedroom/2 bath, midcentury built home, welcomes you with gorgeous terrazzo floors and warm, custom cherry wood built-ins and cabinetry. 2747 Jefferson Circle offers the perfect blend of comfort, versatility, and a prime location. You will also enjoy a bonus/flex room that currently serves as an office but could easily be a studio, home gym, or third bedroom. The 2 car attached garage is air-conditioned space, providing additional climate controlled storage. Step outside, and you'll find not one, but TWO screened lanais—one leading to a serene backyard and BBQ area and the other feels like a dreamy, sunny greenhouse. Step into the spacious backyard and you will find a 400 square foot detached, air-conditioned garage currently used as a workshop and office. Dreaming of an accessory dwelling unit (ADU) or mother in-law suite? This detached workshop, with its own separate, gated driveway and entrance, is ready for your transformation. This home can adapt effortlessly to all your needs. Inside the home, recent updates will provide you with peace of mind. Impact windows were installed in 2019. No cast iron here! Plumbing and supply lines were replaced in 2016, and a new AC was installed in 2023. It doesn’t get much better than living in the heart of Sarasota. Relish in being just 2.5 miles from the powder-soft sands of Siesta Key Beach and live just minutes from the vibrance of Downtown Sarasota. You can delight in world-class beaches, world class dining, shopping, and cultural experiences all within minutes. Plus, a Sarasota locals favorite, Arlington Park, is merely a 4 minute bike ride OR 4 minute drive and less than 15 minute walk away, offering access to a public pool, tennis courts, racquetball, and shady walking trails. This is more than just a home; it’s your ticket to the ultimate Sarasota lifestyle.
Listing Agent: Worth Fiers Iii (941-812-3380)
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