Location: Sarasota
Do Not Show Listings
2669 STAR APPLE WAY, SARASOTA, FL 34240
$499,00046 Days on yellowkey MLS ID: A4692180
REDUCED by $18,500 (3.6%) on 06/02/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1536 Built: 2021Monthly Fee: $267 Tax: $6,203 (2025)Community: Windward At Lakewood RanchSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,203
Elementary School: Tatum Ridge Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: McIntosh Middle
Remarks: PRICE IMPROVEMENT! Discover exceptional value in this beautifully upgraded 3-bedroom, 2-bath residence located in the highly desirable Windward at Lakewood Ranch community. Built in 2021 and meticulously maintained, this move-in-ready home combines modern design, premium upgrades, and effortless Florida living. An ASSUMABLE 3.62% MORTGAGE presents a rare opportunity for qualified buyers in today's market. Step inside to an inviting open-concept layout highlighted by elegant crown molding throughout the main living areas, dining space, kitchen, and stunning coffered ceiling detail. Thoughtfully designed for modern living, raised outlets have been installed in the living room, bedrooms, and lanai, creating a clean and seamless setup for wall-mounted televisions. The chef-inspired kitchen features quartz countertops, stainless steel appliances, under-cabinet lighting, generous cabinetry, and ample workspace for entertaining or everyday enjoyment. The spacious primary suite serves as a private retreat, complete with two oversized walk-in closets and a well-appointed en-suite bath featuring dual vanities and a walk-in shower. Outdoor living is equally impressive. Relax on the extended screened lanai overlooking a fully fenced backyard enhanced by privacy landscaping and a custom travertine patio—perfect for a fire pit, outdoor gatherings, or simply enjoying Florida's beautiful weather. Additional features include an extended garage with utility sink, pull-down attic access with additional floored storage, ceiling-mounted garage storage racks, and recently cleaned, sanded, and sealed paver driveway and walkways. Every window is outfitted with white wood blinds, while the rear sliding doors feature added vertical blinds for privacy and convenience. Most furnishings are negotiable, offering a turnkey opportunity for buyers seeking flexibility. Garage cabinetry and workbench may also be included. Residents enjoy access to Windward's resort-style amenities, including gated entrances, community pools, fitness center, clubhouse, tennis courts, pickleball, and more. Conveniently located just minutes from Lakewood Ranch Main Street, Waterside, UTC shopping and dining, I-75, and the Gulf Coast's renowned beaches. Offering an outstanding combination of location, upgrades, lifestyle, and value, this home is ready for its next owner. Schedule your private showing today.
Listing is courtesy of: KW SUNCOAST (941-792-2000)
Listing Agent: Gerry Tomchinsky (941-577-5184)
1817 6 TH ST, SARASOTA, FL 34236
$999,99928 Days on yellowkey MLS ID: A4694609
0 Days Off yellowkey (back on 6/16/2026)
REDUCED by $95,001 (8.7%) on 06/12/2026
Bed: 8 Bath: 3.0 Liv Area Sq Ft: 2211 Built: 1932 Tax: $12,519 (2025)Community: Gillespie Park SubSpa: NoSingle Family
Taxes:$12,519
Elementary School: Alta Vista Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Under contract-accepting backup offers. Build your downtown Sarasota legacy on one of the largest and most strategically positioned parcels to come to market in Gillespie Park in years. This rare ±19,400 SF double lot (100' x 194') sits in the heart of one of Sarasota's most actively transforming neighborhoods, offering a blank canvas for contractors, custom builders, developers, and end users ready to capitalize on the city's most compelling infill corridor. DTN (Downtown Neighborhood) zoning allows for this ±0.45-acre site the potential to support approximately 5 residential units, a luxury single-family estate, a multi-generational compound, or a boutique townhome project (buyer to verify all uses with the City of Sarasota). The two combined lots create a 100-foot-wide buildable footprint that is extraordinarily rare at this proximity to downtown. Located in Flood Zone X, the property carries no mandatory flood insurance requirement and faces none of the elevation and construction cost burdens that affect so much of coastal Sarasota — a significant competitive advantage for any development pro forma. The site is clean and ready for permitting. Gillespie Park is not an emerging neighborhood — it has arrived. Adjacent to the Rosemary District (Sarasota's most walkable neighborhood with a Walk Score of 88), the area is surrounded by completed and ongoing new construction. Residents walk to Main Street dining, the Sarasota Farmers Market, Whole Foods, Sprouts, Regal Cinema, the Van Wezel Performing Arts Hall, and The Bay — Sarasota's transformative 53-acre waterfront park. Siesta Key Beach is approximately 20 minutes away. Opportunities to acquire nearly half an acre with this zoning flexibility, this location, and this lot dimension do not come along often. Whether you are a developer looking for your next high-margin project or a buyer ready to build a custom urban oasis, this is the site.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Vincent Lamaida (941-416-5654)
3927 DESOTO RD, SARASOTA, FL 34235
$725,00074 Days on yellowkey MLS ID: A4689010
REDUCED by $24,000 (3.2%) on 05/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1782 Built: 1983Monthly Fee: $13 Tax: $3,686 (2025)Community: Desoto PinesSingle Family
Taxes:$3,686
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. PRICE REDUCED!!!!Set on an expansive 1.06-acre lot, 3927 DeSoto Road in Sarasota offers a rare combination of space, privacy, and versatility. The oversized parcel provides endless possibilities—whether you envision lush landscaping, additional structures, or simply enjoying the open room to spread out. At the heart of the outdoor space is a huge pool, perfect for entertaining, relaxing, or creating a true backyard retreat. With this much land surrounding it, the pool area feels private and resort-like, offering plenty of room for outdoor seating, dining, and recreation. Inside, the home features a spacious interior layout with generous living areas designed for comfort and functionality. Large rooms, open flow, and abundant natural light create an inviting atmosphere that’s ideal for both everyday living and hosting guests. This property stands out for its rare lot size, impressive outdoor amenities, and roomy interior, making it a unique opportunity in Sarasota for anyone looking for space without sacrificing convenience. Home is located very close to UTC, Benderson Park and all local beaches and downtown Sarasota.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Gabe Gadah (941-376-4229)
3988 LOSILLIAS DR, SARASOTA, FL 34238
$1,575,00024 Days on yellowkey MLS ID: OM725373
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4840 Built: 1988Monthly Fee: $323 Tax: $13,005 (2025)Community: PrestanciaSpa: YesSingle Family
Taxes:$13,005
Remarks: Nestled behind the gates of one of Sarasota’s most established neighborhoods, this Prestancia home offers quiet luxury and golf course views, where expansive indoor and outdoor living spaces epitomize Florida-living. The thoughtfully designed layout boasts a private master wing on one side, and casual living areas and additional bedrooms on the opposite. Joining the two wings are a formal dining and living room, distinguished by high ceilings, transom windows, and sliding doors which lead to an inviting outdoor retreat. The grand, master suite includes a dressing area, large walk-in closets, and a convenient, wall-enclosed dog yard for pets to safely enjoy. The adjoining master bath hosts separate custom vanities, a Roman walk-in shower, and a water-closet equipped with a hands-free electronic toilet/bidet. Just beyond the spa tub, double French doors open onto a secluded outdoor gathering space complete with a fireplace, perfect for unwinding on cozy evenings. The spacious kitchen is well suited for preparing both gourmet meals and quick refreshments served through the pass-through sliding windows that open to the outdoor eating area. Adjacent the kitchen is a large family room with soaring ceilings, a stone fireplace, and full wet bar. The outdoor oasis is bordered by the home on three sides and the 3rd hole of TPC Prestancia on the fourth, and includes a sparkling pool and spa, integrated grill, shaded area for dining and plenty of space to enjoy Florida sunshine. Residents of this Audubon Cooperative Sanctuary community enjoy watching families of sandhill cranes while bald eagles soar overhead. Just minutes from Siesta Key Beach and downtown Sarasota, the home’s new roof, pull down storm shutters, and a whole home generator provide worry-free living. Optional membership is available at TPC Prestancia Golf Club featuring two 18-hole courses, dining, and social activities.
Listing is courtesy of: BLUE MAGNOLIA REAL ESTATE LLC (352-441-0743)
Listing Agent: Heidi Jasper (352-441-0743)
7524 WESTMORELAND DR, SARASOTA, FL 34243
$5,500,0009 Days on yellowkey MLS ID: A4695898
Bed: 6 Bath: 5.5 Gar: 5 Liv Area Sq Ft: 6215 Built: 2001 Tax: $15,233 (2025)Community: Whitfield Estates Unit 1Spa: NoSingle Family
Taxes:$15,233
Elementary School: Florine J. Abel Elementary
High School: Bayshore High
Middle School: Electa Arcotte Lee Magnet
Remarks: Set on a premier waterfront lot in the Sarasota/Bradenton area, this single-family estate offers panoramic water views, a separate guest house, and the kind of indoor-outdoor living buyers expect at the luxury level. The main residence (3806 sq ft) is designed for entertaining and everyday comfort, with expansive living spaces, a well-appointed kitchen, and seamless access to the pool and outdoor areas, while the guest house (2409 sq ft) provides ideal accommodations for visitors, extended family, or a private office retreat. Comfortable luxury living on a combined 1+ acre lot (there are 2 parcels included in this offering) with a spectacular panoramic water view. Beautifully kept grounds accented by Royal palms create the feel of a family compound that elegantly states, "You've made it!" The three-story main house has a twin grand winding staircase and an elevator to the second-floor main level. Tall double-trey ceilings w/ uplighting and massive impact glass windows and doors provide an absolutely breathtaking view of the swimming pool and the Sarasota Bay. Built on 38 concrete and steel reinforced pilings, the main house was constructed in 2001, and the windows and doors were upgraded to hurricane standards. In fact, the owner has a flood policy on the main house for just $1,200 per year. There is an oversized 3 car garage with an expanded work area and 220V power if you have an electric car. Plus, a massive unfinished storage and fun area with non-conforming pool bath below the main living area elevated approximately 18' above. The completely separate guest house also with views of the bay includes an additional 3 bedrooms, great room, dining room, full kitchen, office and attached 2 car garage. The guest house was built in 1950 and remodeled to mimic the Coastal Mediterranean style of the main house. The pool ranges from 3' to 7' in depth and includes remote control lighting and a water feature. The pool and outdoor area create the perfect setting for parties or special events. The pool is surrounded by a huge concrete deck that extends as a patio under the cover of the massive main observation and entertainment deck above. There are rough ins for an outdoor kitchen on the ground floor patio. There is also an additional observation deck off the 3rd floor living room that, with a slight zoom on your camera, provides a nice view of John Ringling bridge. Longboat Key provides night lights beyond the bay, and your own private Osprey nest adds to the natural symphony of life on the water. Boaters, you are less than a mile away from Sara Bay Marina. Commuters, you are less than 3 miles away from SRQ. Beach goers, you are less than 10 miles from Lido Beach and St Armands Circle. Professionals, you are less than 7 miles from downtown Sarasota. Kayakers, walk to the Riprap and launch! Be sure to watch the individual videos showing each interior. They are not just slideshows. This is the first time this property has been offered for sale since the builder owned it. An acre of mainland bayfront land is rare in the Sarasota/Manatee waterfront community. Don't Daydream and miss out on your Dream home. The main home is being sold partially furnished with a few exclusions. The guest house is unfurnished. Capture the Zen of waterfront living for yourself and future generations now.
Listing is courtesy of: FLORIDA INTERNET REALTY LLC (941-961-4983)
Listing Agent: Steve Rider (941-504-5163)
411 BURNS COURT, SARASOTA, FL 34236
$1,075,00028 Days on yellowkey MLS ID: A4694679
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1345 Built: 1926 Tax: $4,644 (2025)Community: Burns Court Sub OfSingle Family
Taxes:$4,644
Elementary School: Southside Elementary
Remarks: Under contract-accepting backup offers. This iconic commercial/residential Burns Court bungalow, the ultimate live/work space, offers a rare opportunity to restore and personalize a truly unique downtown property in one of Sarasota's most coveted historic neighborhoods. The Burns Ct. facing 2-bedroom, 1-bath main residence features a private masonry-walled back courtyard leading to a large 1-bedroom, 1-bath detached unit. This unit, with frontage on Pineapple Avenue, is ideal for commercial or residential use, a guest apartment, private office/studio, small shop... Located in the heart of nationally designated Historic Burns Court, one of downtown Sarasota’s most walkable neighborhoods, the property is just steps from an award-winning cinema, restaurants, boutiques, and the Bayfront, yet notably outside of a flood zone. Many original architectural details remain intact, including decorative ironwork, moisture-resistant plaster walls, crown molding, and original hardwood floors. A beautiful, mature oak tree provides valuable shade and enhances the home’s historic charm. The home has excellent bones for a dream restoration project, the main house featuring a 2023 roof and 2019 HVAC. Built-in equity: Zoned Downtown Core (DTC), the property includes confirmed transferable development rights (TDRs), which may be sold to a developer or investor thanks to a new historic preservation ordinance effective as of December 2025. Whether you envision creating a stunning live/work environment, generating income from a detached apartment, or designing an elegant commercial space, this charming property offers exceptional flexibility and historic character.
Listing is courtesy of: CHROME REALTY LLC (941-363-6300)
Listing Agent: Erin Difazio (941-870-8060)
1356 POINT CRISP RD, SARASOTA, FL 34242
$4,495,00044 Days on yellowkey MLS ID: A4692551
2 Days Off yellowkey (back on 5/12/2026)
Bed: 5 Bath: 5.5 Gar: 6 Liv Area Sq Ft: 7443 Built: 2005 Tax: $61,095 (2025)Community: Point Crisp AddSpa: YesSingle Family
Taxes:$61,095
Remarks: Virtually Staged. Ideally positioned on the exclusive Point Crisp Peninsula of Siesta Key, this waterfront estate offers a rare blend of privacy, scale, and direct boating access, with sweeping views spanning both Little Sarasota Bay and the Intracoastal Waterway. Set on over 230 feet of water frontage, the property features a newly constructed T-shaped dock (2025) and allows for effortless arrival by land or water, all complemented by the rare advantage of nearby beach access. Spanning more than 7,400 square feet of interior living space, the five-bedroom residence is designed for elevated coastal living, where expansive entertaining areas and walls of glass frame panoramic water views throughout. Freshly painted and ready for personal customization, the two-story interior is defined by high coffered and tray ceilings, crown molding, solid-core doors, and a blend of marble and wood flooring. A grand double-door entry opens to a soaring living area with a cathedral ceiling and statement fireplace, while floor-to-ceiling sliding glass doors create a seamless connection to the outdoor living spaces. The multi-level outdoor setting is designed for both gathering and relaxation, featuring an extended travertine deck, covered lounge areas, an outdoor gas fireplace, a summer kitchen with built-in grill and wraparound bar, an additional grilling station, and a heated pool and spa—all overlooking the tranquil waterfront. At the center of the home, the gourmet kitchen was redesigned in 2022 with quartzite countertops, custom cabinetry, professional-grade appliances, and an oversized island with seating. The adjacent family room offers built-in features and direct access to the outdoor entertaining areas, creating a natural flow for everyday living. The primary suite, located on the main level, serves as a private retreat with expansive water views, a custom walk-in closet, and a spacious en-suite bath. An additional guest suite on this level provides flexibility for a study, fitness room, or nursery. The second level is dedicated to guest accommodations and recreation, offering a home theater, an oversized game room with wraparound bar, multiple terraces, and three additional bedroom suites—one of which is generously scaled to function as a second primary suite—each with access to outdoor living spaces. The ground level includes a six-car split garage with multiple storage and utility rooms, supporting both functionality and flexibility. Located within one of Siesta Key’s most sought-after enclaves, this residence offers the unique combination of close beach access and protected boating waters. Just minutes away, Siesta Key Village provides dining and boutique shopping, while downtown Sarasota offers a vibrant cultural scene with theaters, galleries, waterfront parks, and marinas—delivering a lifestyle that balances coastal tranquility with everyday convenience.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
3711 HIDDEN RIVER RD, SARASOTA, FL 34240
$750,00063 Days on yellowkey MLS ID: A4690484
1 Days Off yellowkey (back on 4/22/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2164 Built: 1973 Tax: $5,521 (2025)Community: Hidden RiverSingle Family
Taxes:$5,521
Remarks: Under contract-accepting backup offers. A rare opportunity to own nearly 10 acres in one of Sarasota’s most unique aviation communities, offering the ultimate blend of privacy, space, and lifestyle. With direct access to a private airstrip, this property is ideal for aviation enthusiasts seeking the convenience of keeping their aircraft just steps from home. Set on expansive, picturesque land, the property features a private hangar, allowing for seamless fly-in, fly-out access, along with a tennis court and a variety of existing structures including a barn, stable, greenhouse, and additional outbuildings—creating endless possibilities for recreation, storage, or hobby use. The existing 3-bedroom, 2-bathroom block home offers over 2,100 square feet of living space and presents a prime opportunity for a buyer to update, renovate, or reimagine the space to their vision. Being sold as-is, the home provides a strong foundation with solid construction, making it an ideal option for investors or those looking to create a custom estate without starting from scratch. Surrounded by mature trees, natural landscape, and peaceful water views, the setting feels like a private retreat while still being conveniently located to town. Whether you’re looking to restore and personalize the existing home, build your dream estate, or create a private aviation retreat, this property offers a rare combination of land, flexibility, and lifestyle in a highly sought-after location.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Katie Cobb (913-744-0248)
558 VENICE LN, SARASOTA, FL 34242
$4,485,00070 Days on yellowkey MLS ID: A4689132
REDUCED by $164,900 (3.5%) on 06/16/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4132 Built: 2025Monthly Fee: $33 Tax: $4,509 (2025)Community: Siestas Bayside Waterside EastSpa: YesSingle Family
Taxes:$4,509
Elementary School: Phillippi Shores Elementary
High School: Riverview High
Middle School: Brookside Middle
Remarks: Newly completed and move-in ready, this Coastal Contemporary waterfront residence on Siesta Key by award-winning Heritage Builders offers 4,132 sq ft with 5 bedrooms, 4.5 baths, a private study, loft, and elevator—perfectly blending luxury, functionality, and coastal living. The main level features white oak wood floors, soaring beamed ceilings, and a bright open-concept layout designed for both everyday living and entertaining. The gourmet kitchen and expansive great room flow seamlessly through 10’ impact-resistant sliding glass doors to the outdoor living area, showcasing tranquil views of the pool and Grand Canal. A dedicated private office, a luxurious primary suite with a spa-inspired bath, and an additional ensuite guest bedroom complete the first floor. Upstairs, a spacious loft provides an ideal secondary gathering space. The VIP suite features a private balcony overlooking the water, while the fifth bedroom offers flexibility as a media room, fitness studio, or guest retreat. A custom wet bar enhances the upper level, creating the perfect setting for entertaining. Set along the scenic canals of Siesta Key, this property offers exceptional boating opportunities with easy access to open water—ideal for enjoying the best of Florida’s waterfront lifestyle right from your backyard. The outdoor living space is designed as a private retreat, complete with a sparkling pool, spa, and peaceful water views. Quick out to the expensive Intracoastal waterways for boaters. Florida living at its finest — sunset views, alfresco dining, and cozy evenings by the outdoor fireplace. A beautiful patio and grill setup that feels like a dream come true. Located just minutes from Siesta Key Beach, this home provides quick access to world-renowned beaches, dining, and the vibrant coastal lifestyle that makes Siesta Key one of the most desirable destinations in Florida. Exceptional opportunity to own a brand-new waterfront home with boating access in one of Sarasota’s premier locations.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Andrew Haddad (941-313-1218)
4079 LAS PALMAS WAY, SARASOTA, FL 34238
$1,699,000114 Days on yellowkey MLS ID: A4683982
REDUCED by $50,000 (2.9%) on 05/30/2026
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 5073 Built: 1988Monthly Fee: $73 Tax: $14,847 (2025)Community: PrestanciaSingle Family
Taxes:$14,847
Elementary School: Gulf Gate Elementary
Middle School: Sarasota Middle
Remarks: Nestled behind the gates of Prestancia, one of Sarasota’s most established and sought-after golf communities, this exceptional estate offers the perfect blend of timeless elegance, privacy, and opportunity. Situated on an oversized and beautifully landscaped homesite of nearly 0.8 acres, the residence spans approximately 5,073 square feet and is thoughtfully designed for both grand-scale entertaining and comfortable everyday living. A dramatic arrival sets the tone, with soaring ceilings, expansive living spaces, and walls of glass that fill the home with natural light while showcasing tranquil views of the lush surroundings. Offering four spacious bedrooms, multiple living and gathering areas, and four-plus baths, the flexible floor plan easily accommodates guests, multigenerational living, a dedicated home office, fitness space, or creative studio. The home's generous proportions create an effortless flow between formal and casual living areas, while the outdoor spaces invite year-round enjoyment of Sarasota’s coveted indoor-outdoor lifestyle. Mature landscaping and exceptional lot size provide a level of privacy rarely found in today's market. Additional highlights include a three-car garage, generously sized en-suite bedrooms, abundant storage, and the quality craftsmanship associated with Prestancia’s premier estate residences. Located within Palmer Ranch, residents enjoy convenient access to world-famous Siesta Key Beach, championship golf, the Legacy Trail, fine dining, upscale shopping, downtown Sarasota, and the area's vibrant arts and cultural scene. With its impressive scale, premier location, and endless potential to personalize and elevate, this is a rare opportunity to secure a signature estate within one of Sarasota's most prestigious gated communities.
Listing Agent: Nikki Taylor (941-587-9060)
1150 52ND ST, SARASOTA, FL 34234
$355,00058 Days on yellowkey MLS ID: O6400956
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1136 Built: 1959 Tax: $3,097 (2025)Community: Armstrong Acres Surv Lt 1 RSingle Family
Taxes:$3,097
Elementary School: Emma E. Booker Elementary
Remarks: Experience the quintessential Florida lifestyle in this charming coastal retreat located in the desirable Desoto Lakes community. This beautifully maintained residence captures the essence of Sarasota living with a bright, open interior that seamlessly blends comfort and style. The heart of the home features a spacious living area that flows effortlessly into a functional kitchen, perfect for both casual morning coffee and evening entertaining. The split floor plan ensures maximum privacy, highlighted by a serene primary suite and well-appointed guest bedrooms. Step through the sliding glass doors to discover your private outdoor oasis—a generous, fenced-in backyard that offers the ideal canvas for a lush tropical garden, a future pool, or weekend gatherings under the Florida sun. Notable features include a durable exterior, an attached garage for convenient storage, and a prime location that places you just minutes from the world-class shopping and dining at University Town Center. With easy access to the pristine sands of Siesta Key and Lido Beach, as well as the vibrant arts scene of downtown Sarasota, this home offers an incredible opportunity to own a piece of paradise.
Listing is courtesy of: HOUWZER INC (267-765-2080)
Listing Agent: Daniel Robinson (904-447-8922)
1732 SHORELAND DR, SARASOTA, FL 34239
$1,995,000125 Days on yellowkey MLS ID: A4682616
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3790 Built: 2018 Tax: $20,697 (2025)Community: Shoreland Woods SubSpa: YesSingle Family
Taxes:$20,697
Remarks: Under contract-accepting backup offers. Welcome to modern West of Trail living — where space, style, and location come together in one of Sarasota’s most desirable family neighborhoods. Designed for the buyer who wants room to grow without sacrificing lifestyle or convenience, this stunning newer construction home offers the perfect balance of luxury, functionality, and everyday ease. From the moment you arrive, the quiet, tree-lined streets and classic white-picket-fence charm of the neighborhood set the tone. Surrounded by multi-million-dollar homes and a true community feel, this is the kind of place where families ride bikes in the evenings, walk to school, and enjoy a relaxed yet refined Sarasota lifestyle. Step through the front door and into a dramatic, light-filled foyer that immediately showcases the home’s modern aesthetic and open, airy design. Soaring ceilings, sleek lines, and expansive glass create a sense of volume and energy, while the open-concept floor plan delivers the flexibility today’s families need. The main living space flows effortlessly into a designer kitchen featuring an oversized island, premium appliances, custom cabinetry, and abundant storage — ideal for casual family dinners or entertaining friends. With five bedrooms plus a dedicated office and a spacious bonus room/loft, this home was designed around real life. Whether you need guest space, a media room, playroom, or homework zone, there is room for everyone to spread out while still feeling connected. One of the most unique features is the flexibility of having a choice of a primary suite on the first or second floor, making the home ideal for multi-generational living, long-term flexibility, or simply choosing the layout that best fits your lifestyle. Outside, the lifestyle continues. The heated pool and outdoor kitchen create an effortless indoor-outdoor flow perfect for weekend gatherings or quiet evenings at home. Unlike many tropical properties, the landscaping is intentionally low-maintenance, giving you the beauty of a resort-style setting without endless upkeep — more time enjoying, less time working. Built above the flood plain, this home offers an important advantage for peace of mind and long-term savings: no flood insurance required. Modern construction standards, quality materials, and hurricane-rated features ensure durability and efficiency for years to come. Location is everything, and this one is hard to beat. Walk to highly rated Southside Elementary and the boutiques and restaurants of Southside Village. Enjoy dinner just a block away at some of Sarasota’s most loved restaurants. Spend your weekends at Siesta Key Beach or downtown Sarasota — both just about eight minutes away — then return home to a quiet, suburban setting that feels private, safe, and unmistakably family-friendly. This is more than just a beautiful modern home — it’s a lifestyle designed around space, comfort, and connection in one of Sarasota’s most coveted neighborhoods. If you’ve been searching for a move-in-ready home with bedrooms to spare, a pool, modern design, and a location that checks every box, this is the one. Schedule your private showing and experience West of Trail living at its best.
Listing is courtesy of: EXP REALTY LLC (800-486-1794)
Listing Agent: Mark Coppens (941-444-0436)
6100 HOLLYWOOD BLVD, SARASOTA, FL 34231
$649,00042 Days on yellowkey MLS ID: A4692788
REDUCED by $50,000 (7.2%) on 06/05/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2325 Built: 1956 Tax: $3,185 (2025)Community: Aqualane Estates 2NdSpa: NoSingle Family
Taxes:$3,185
Remarks: Located in the highly desirable Aqualane Estates, just about a mile from the world-famous Siesta Key Beach and Crescent Beach, and close to local favorite Captain Curt’s Crab & Oyster Bar, this unique property offers an incredible opportunity to own in one of Sarasota’s most sought-after waterfront neighborhoods. Surrounded by million-dollar homes and picturesque canal-lined streets, the setting alone makes this home truly special. Set on an expansive 0.40-acre lot, the property is anchored by a stunning, majestic banyan tree that creates unmatched curb appeal and Old Florida charm. While the home does not offer full canal access, it does feature a small sliver of water frontage, adding to its character. With no HOA, you’ll enjoy added flexibility and freedom rarely found in such a prime location. Additionally, the home is in Flood Zone X and X500 and has never flooded. This oversized lot also presents exceptional potential for redevelopment, with ample space to build a new custom home in line with the luxury properties throughout the neighborhood—making it ideal for investors, builders, or buyers looking to create their dream home. Built in 1956, this classic Florida-style home offers 3 bedrooms, 2 bathrooms, and 2,325 square feet of living space. Inside, you’ll find timeless character throughout, including beautiful terracotta tile flooring accented with unique hand-painted tiles, along with artistic touches carried into the primary bedroom and shower. The outdoor space is designed for enjoying the Florida lifestyle, featuring a large, private pool ideal for laps, all enclosed within a fenced backyard and patio area for added privacy. A two-car garage with an attached workshop provides plenty of room for storage, hobbies, or projects. Recent updates include a 2025 shingle roof and an upgraded lift station for the septic system, offering peace of mind for the next owner. Whether you’re looking to enjoy it as-is, renovate, or build new, this property offers a rare combination of location, lot size, flexibility, and future potential just minutes from the beach, dining, and everything Sarasota has to offer.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Roni-Marie Gold, Pa (941-487-0105)
5309 CHARLIE BROWN LN, SARASOTA, FL 34233
$749,00041 Days on yellowkey MLS ID: A4691590
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2768 Built: 2016Monthly Fee: $261 Tax: $6,961 (2025)Community: Luna BaySpa: NoSingle Family
Taxes:$6,961
Elementary School: Ashton Elementary
Remarks: Opportunities like this are rare in Luna Bay, an intimate Sarasota neighborhood of just 21 homes—offering a true sense of privacy and community that’s hard to find. This beautifully appointed 4-bedroom, 3.5-bath residence is offered fully furnished, making it completely turnkey for immediate enjoyment or investment. The open floor plan features a desirable downstairs primary suite, a den/office and an upstairs loft ideal for a playroom, study area, or TV room. From the moment you arrive, the barrel tile roof, paver driveway, and covered front porch create impressive curb appeal. Inside, the home is bright and inviting with wood cabinetry, granite countertops, generous closet space, and numerous upgrades throughout. Step outside to a south-facing covered lanai overlooking the screened, heated pool with a paver deck, all set within a fenced backyard that offers complete privacy—perfect for relaxing, entertaining, or pets. Enjoy a low-maintenance lifestyle with HOA-covered yard maintenance. Ideally located within the highly sought-after Ashton Elementary school district and just minutes from top-rated Sarasota schools, this home also offers exceptional proximity to Siesta Key Beach, I-75, and a wide array of shopping and dining options. This is a rare opportunity to own a fully furnished home in a boutique community in one of Sarasota’s most desirable locations.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Mark Quire (941-993-5706)
2959 N LOCKWOOD MEADOWS BLVD, SARASOTA, FL 34234
$380,00067 Days on yellowkey MLS ID: TB8493921
REDUCED by $4,900 (1.3%) on 05/28/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 924 Built: 1985 Tax: $3,867 (2025)Community: Lockwood MeadowsSpa: NoSingle Family
Taxes:$3,867
Remarks: ** NEW PRICE IMPROVEMENT ** Best single family offering in Sarasota at an affordable price - Beach life? Siesta Key 10-15 min, Lido 7-10, Longboat 15-20. Schools 5 minutes! UTC Mall and Rt 75 are 10-12 minutes away. Downtown restaurants in 10 minutes. Want move in ready? 1 car garage, full shed in back yard. Want updates? Roof 2025, Water Heater 2025, AC and Ducts just replaced 2 months ago. Washer and dryer less than 3 yrs old. Full master bath and Walk in shower, new fridge and soft close cabinets. Want Florida living? Fire pit, Bermuda Cherry, Orange, Lime, Lemon, Tangelo, and Red Lime trees should bear fruit this year. 12 ftx 36 ft screened lanai for grilling and back yard lounging. Back yard is completely fenced. Room for a pool. No HOA! Established neighborhood NEVER WET! No storm damage history.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Leah King (813-957-8924)
8458 SNOWFALL ST, SARASOTA, FL 34241
$1,889,000105 Days on yellowkey MLS ID: A4685211
1 Days Off yellowkey (back on 6/16/2026)
REDUCED by $106,000 (5.3%) on 05/01/2026
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4562 Built: 2024Monthly Fee: $251 Tax: $16,228 (2025)Community: Skye Ranch Nbrhd ThreeSpa: YesSingle Family
Taxes:$16,228
Elementary School: K-8 At Clark And Lorriane
Remarks: Under contract-accepting backup offers. Welcome to 8458 Snowfall Street, an exceptional residence completed in 2024 and located in the highly sought-after Skye Ranch community of Sarasota, where luxury living meets a vibrant, family-oriented neighborhood and outstanding resort-style amenities. This impressive home offers 4 bedrooms, 4 full bathrooms, and 2 half baths across a spacious, thoughtfully designed floor plan that balances comfort, style, and functionality. The residence includes the primary bedroom on the first floor, a private office and a dedicated media room and in-law-suite on the second floor providing flexible spaces for work, entertainment, and everyday living. Expansive open living areas are filled with natural light and designed for effortless entertaining, seamlessly connecting the interior living spaces with the outdoor retreat. Outdoor living is truly resort-inspired. The expansive 1400 square ft. lanai features an oversized pool and spa, along with a fully equipped outdoor kitchen, fire pit and golf putting green creating the perfect setting for hosting gatherings or enjoying relaxing evenings in your private backyard oasis. Beyond the home itself, residents of Skye Ranch enjoy one of Sarasota's most dynamic master-planned communities. At the heart of the neighborhood is The HUB Amenity Center, where families gather to enjoy a resort-style pool and splash pad, fitness center, basketball court, climbing wall, clubhouse and café, sports courts, playgrounds, dog park, and over 23 miles of scenic walking and biking trails woven throughout beautiful natural preserves. The HUB also hosts a lively calendar of community events, family activities, movie nights, and seasonal celebrations, creating a warm and welcoming environment where neighbors quickly become friends. Ideally located near the new Skye Ranch K-8 School and just minutes from I-75, shopping, dining, and Sarasota's world-renowned Gulf Coast beaches, this remarkable home offers the perfect balance of luxury, recreation, and community connection.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Stacey King (646-734-5014)
119 AVENIDA MESSINA, SARASOTA, FL 34242
$5,450,000360 Days on yellowkey MLS ID: A4656843
Bed: 7 Bath: 8.0 Gar: 2 Liv Area Sq Ft: 3600 Built: 2023 Tax: $15,412 (2025)Community: Mira Mar BeachSingle Family
Taxes:$15,412
Remarks: Luxury Living in the Heart of Siesta Key! This beautifully designed coastal retreat offers 7 bedrooms, 7 full bathrooms, and 2 half baths, providing plenty of space for hosting family and friends in total comfort. Every detail was thoughtfully crafted to blend high-end design with relaxed Florida living. The main living area is open, airy, and filled with natural light, creating an effortless flow for both everyday life and entertaining. A private elevator makes accessing all levels a breeze, while wraparound balconies and large windows showcase the lush, tropical surroundings. At the center of the home, the chef’s kitchen features a gas range, oversized island, and ample seating—perfect for gathering, cooking, and connecting. Step outside and you’ll find your own private escape: a heated pool and spa, putting green, and a spacious patio designed for making the most of every sunny day. Whether you're lounging poolside or enjoying a casual game of ping pong, this outdoor space was made for fun and relaxation. Upstairs, the second level includes three luxurious king suites with private en-suite baths. The third floor offers four additional bedrooms—three more king suites and a bunk room with two full-over-full bunks, making it ideal for large families or groups. At the top of it all, the rooftop terrace delivers incredible views of Siesta Key Village and the nearby beach. It’s the perfect spot to take in the sunset, sip a cocktail, or stargaze late into the evening. A built-in wet bar completes the experience. This is a rare opportunity to own a one-of-a-kind home in one of Siesta Key’s most coveted locations. With stunning finishes, thoughtful amenities, and a true resort-style feel, this residence offers coastal living at its finest. Schedule your private tour today.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Curt Ware (941-587-9122)
7151 WAINSCOTT CT, SARASOTA, FL 34238
$959,90017 Days on yellowkey MLS ID: A4695421
1 Days Off yellowkey (back on 6/11/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3054 Built: 2001Monthly Fee: $181 Tax: $6,320 (2025)Community: The HamptonsSpa: YesSingle Family
Taxes:$6,320
Middle School: K-8 At Clark And Lorriane
Remarks: Welcome to West Hampton, a quiet gated enclave of just 57 high quality residences in popular Palmer Ranch. This beautifully updated 4 bedroom plus den/office, 3 bath home is located on one of the most desirable waterfront cul-de-sac lots in the community, with a panoramic view of nature from the pool and lanai, as well as from the interior living space.The features and upgrades in this home will allow you to check off nearly everything on your “must have” list. The new flat tile roof (12/2024) is just one of many items that make this home “better than new.” As you enter, you will immediately recognize the classic split floor plan, with the den to your left and the living and dining rooms ahead and to your right. Take note of the beautiful ceramic plank floors which run throughout the home, then look ahead to the view of the pool and spa, and the pond beyond. The owners have creatively reimagined this space, providing a formal dining area that takes full advantage of the view. The primary suite is to your left, where you will find an updated en suite bathroom with separate sinks, a dressing table, tub and walk-in shower. The bedroom features a walk in closet and a second large closet, and of course, a view of the pool and pond and access to the lanai. Pass through the center of the home to the combined kitchen/family room, where you will still enjoy the full view of the pool and lanai. The kitchen will satisfy the needs and desires of those who love to cook, with plenty of cabinet space, a new double wall oven (with convection), oversized LG refrigerator, and Wolf gas cook top. A built-in desk and china cabinet are located in the adjoining dinette. Beyond the family room to the rear of the home you will find a 14'x19' guest suite which provides an en suite bathroom, access to the pool, and a picture window overlooking the pond. Two additional bedrooms, a bathroom, the laundry and pantry complete this side of the home. Returning to your “must have” list, you can check off the 3 car garage, two newer HVAC units, natural gas for heating and cooking, brick driveway and lanai, ideal location near beaches, shopping, dining, the city of Sarasota, and more. If good schools are on your list, excellent private and public schools are nearby. Please note that all furniture is available for purchase at buyer's option under separate agreement.
Listing Agent: Charlie Offer (941-321-9664)
4471 TRAILS DR, SARASOTA, FL 34232
$525,000112 Days on yellowkey MLS ID: A4683777
REDUCED by $25,000 (4.5%) on 06/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1721 Built: 1987Monthly Fee: $193 Tax: $3,485 (2025)Community: TimberlakesSpa: NoSingle Family
Taxes:$3,485
Elementary School: Brentwood Elementary
Remarks: ONE OF THE BEST VALUES CURRENTLY AVAILABLE IN THE LAKES. Fresh new price, same incredible lifestyle. Welcome to this beautifully maintained 3-bedroom, 2-bath single-family home in The Lakes, a sought-after community in the heart of Sarasota. Offering 1,721 square feet of comfortable living space, this residence features a thoughtfully designed split-bedroom floor plan that balances privacy with everyday functionality. Enjoy added peace of mind with a 2023 roof and hurricane protection, including impact windows and/or shutters, providing both security and energy efficiency. The spacious living and dining areas flow seamlessly to a screened porch — the perfect spot for morning coffee or relaxing evenings overlooking the private, tree-lined backyard. The serene outdoor setting creates a peaceful retreat with plenty of room to entertain, garden, or simply unwind. Residents of The Lakes enjoy an impressive array of amenities, including one clubhouse and two community pools, tennis and basketball courts, a fitness center, and scenic walking trails. Ideally located in central Sarasota, you’re just minutes from world-class beaches, exceptional dining, premier shopping, and the area’s vibrant cultural attractions.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Mary Pat Phillips Radford (941-587-9905)
1850 WEBBER ST, SARASOTA, FL 34239
$3,790,00084 Days on yellowkey MLS ID: A4686673
REDUCED by $100,000 (2.6%) on 06/16/2026
Bed: 6 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4755 Built: 2026 Tax: $18,011 (2025)Community: Poinsettia Park 2Spa: YesSingle Family
Taxes:$18,011
Remarks: Virtually Staged. West of trail, 2026 Custom Build, Exquisite Modern Mediterranean estate with a seamless blend of classic architecture and contemporary finishes. This exceptional 5-bedroom, 4-bathroom residence is thoughtfully designed for both everyday living and effortless entertaining. The main level features a luxurious first-floor primary suite with a walk-in closet and spa-inspired bathroom with dual vanities, along with two first-floor guest bedrooms and a private office. Wide-plank oak hardwood floors, custom built-ins and maple wood cabinetry with inset doors , and a warm, inviting electric fireplace enhance the home’s elegant yet comfortable ambiance. A fully integrated surround sound system extends throughout the living room, kitchen, and outdoor entertaining areas. The chef’s kitchen is beautifully appointed with premium Viking appliances, Taj Mahal quartzite countertops, custom cabinetry, elevated fixtures and designer lighting, along with a stylish bar featuring Cristallo quartzite and a beverage center—perfect for hosting and entertaining. The second level offers a spacious bonus room ideal for a media lounge or game room, along with two additional bedrooms and a gallery-style hallway with an open balcony, adding architectural interest and natural light. Additional highlights include natural gas, a gas-on-demand water heater, enhanced exterior insulation for energy efficiency, a concrete tile roof, irrigation system, and abundant storage throughout. Architecturally, the home embraces classic Mediterranean elements with a modern sensibility. Arched doorways, windows, and passageways create a sense of flow and understated grandeur, while intricate wrought iron detailing and extensive millwork add depth and craftsmanship. Statement chandeliers and curated designer lighting elevate each space, enhancing the home’s refined aesthetic. A detached guest home, complete with a private bedroom, full bathroom, and living area, offers ideal accommodations for guests or extended stays. Outdoors, a custom-designed oversized pool showcases timeless Mediterranean blue tile, complemented by elegant fire bowls and a cascading waterfall spa—creating a true resort-style setting. The property is complete with a 2-car attached garage in the main home, 2 car covered parking under the guesthouse, and an additional two-car garage, offering both functionality and flexibility. Ideally situated in Southside Village, this residence offers a highly walkable lifestyle just moments from Southside Elementary, Morton's Gourmet Market, local restaurants, and boutique shopping.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Kelly Gettel (941-315-2525)
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