Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
847 FREELING DR, SARASOTA, FL 34242
$3,950,00038 Days on yellowkey MLS ID: A4690268
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4034 Built: 1954 Tax: $40,498 (2025)Community: Bay Island ShoresSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$40,498
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Located in the highly sought-after Bay Isles community on Siesta Key, this property at 847 Freeling Drive offers a rare opportunity to customize and create your ideal coastal home. Positioned on the first street onto Siesta Key, the location provides exceptional convenience to the bridge, mainland, and all that the island has to offer. The home features 4 bedrooms and 4.5 bathrooms, with the upper level remaining intact and in great condition. The ground level experienced flooding during the recent hurricanes; however, the seller has already completed professional remediation, providing a clean slate for updates and renovations to suit your vision. Situated on a protected deep-water basin, the property is ideal for boating and waterfront living, complete with a private dock, no fixed bridges, and direct access just minutes to the Gulf. The home also features a pool, offering the perfect foundation to create a true coastal retreat. This is a unique opportunity to secure a well-located waterfront property and finish it to your exact specifications in one of Siesta Key’s most desirable communities.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Michelle Ward (941-920-2460)
116 GARDEN LN, SARASOTA, FL 34242
$1,995,000206 Days on yellowkey MLS ID: A4671064
REDUCED by $155,000 (7.2%) on 04/20/2026
Bed: 4 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2971 Built: 2017 Tax: $20,113 (2024)Community: Siesta Rev OfSingle Family
Taxes:$20,113
Tax Year: 2024
Remarks: Effortless Island Living on Siesta Key’s Coveted North End. Discover the perfect blend of modern luxury and low-maintenance living in this contemporary coastal retreat, ideally located on the quiet North End of Siesta Key. Enjoy deeded beach access, mesmerizing Gulf and Big Pass views, and effortless proximity to Siesta Village, the North Bridge, and downtown Sarasota. Built in 2017 to the highest standards by MGB—My Green Building—this four-level residence was designed for comfort, efficiency, and peace of mind. Solid construction, energy-smart design, impact-rated materials, and a brand new A/C system (March 2026) make it the ideal lock-and-leave home for those seeking a worry-free coastal lifestyle. Light-filled living spaces flow seamlessly between the gourmet kitchen, dining, and family areas, all centered on the third floor for optimal views and connection. The private primary suite spans the top level with its own balcony retreat, while three guest bedrooms on the second floor offer space for family or friends. An elevator connects all four floors for easy access, and the flexible lower level provides extra room for a fitness area, studio, or media lounge. Designed for those who value quality, comfort, and ease, this home offers all the benefits of coastal living—without the upkeep. From morning beach walks to sunset cocktails overlooking the Gulf, every day here feels like a vacation.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Gerard Healy (941-961-2240)
5618 ASHTON LAKE DR #5618, SARASOTA, FL 34231
$354,900167 Days on yellowkey MLS ID: A4675431
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1233 Built: 1989Monthly Fee: $325 Tax: $3,158 (2024)Community: Ashton Lakes 03Condo
Taxes:$3,158
Elementary School: Gulf Gate Elementary
High School: Riverview High
Remarks: Virtually staged. Welcome to 5618 Ashton Lake Drive, in Ashton Lake Community. A beautifully remodeled first-floor condo offering a spacious open-concept layout with 2 bedrooms and 2 full bathrooms. Thoughtfully updated throughout, the home features modern finishes in timeless neutral tones, creating a bright and inviting atmosphere. The living and dining areas flow seamlessly into the updated kitchen, perfect for both everyday living and entertaining. New hurricane-rated sliders enhance both safety and energy efficiency while framing stunning lake views and allowing abundant natural light, with the convenience of a private one-car garage and easy first-floor access. Nestled in a quiet, two-story building, this condo offers easy access to Ashton Lakes’ resort-style amenities—33 lush acres, 4 scenic lakes, 2 heated pools (one with a lap lane), tennis & pickleball courts, shuffleboard, and a clubhouse. A pedestrian bridge provides direct access to Detwiler’s Market, CVS, and nearby shopping and dining. Conveniently located near I-75 and Route 41, with easy access to shopping, schools, restaurants, and hospitals. This move-in-ready residence combines comfort, style, and tranquility in a highly desirable setting.
Listing is courtesy of: MEDWAY REALTY (941-375-2456)
Listing Agent: Elena Durez (847-338-6413)
4185 S SHADE AVE, SARASOTA, FL 34231
$616,000138 Days on yellowkey MLS ID: A4678362
0 Days Off yellowkey (back on 1/23/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2122 Built: 1990 Tax: $9,222 (2025)Community: Sarasota-Venice Co River SubSpa: YesSingle Family
Taxes:$9,222
Remarks: UNBELIEVABLE OPPORTUNITY! This 3-4 bedroom / 3 bathroom home is directly on Phillippi Creek with a dock and boat lift. This home sits at the very private end of a cul de sac on .5 acres of land! Enter and immediately notice the soaring 15-foot vaulted ceilings & two skylights in the living room with fireplace and handsome stonework all the way up. The rear private patio overlooks greenery. The eat-in kitchen has the same high ceilings and features a central island, quartz tops, raised-panel cabinetry, and a pantry. The 15-foot ceilings carry into the primary bedroom and there is a door out to the rear screened patio, swimming pool, and hot tub. The primary bath features a walk-in closet, dual vanities, and separate shower and soaking tub. There is a separate dining room and split guest bedroom/bath on the main floor as well. Upstairs has a third bedroom, a small bathroom, and fourth bedroom (no closet)-also perfect as an office. Come make this special home all your own with your remodeling ideas and a little TLC! --What the boater's want to know...The dock is older as is the lift. There is a sitting area at the end of the dock for sunrise. It appears to have 3-foot depth under the lift at mean-high tide and it is approximately a relaxing 35-minute boat ride to the Intracoastal Waterway passing under one bridge with approximate clearance of 9.5'. Come see this super waterfront opportunity today at an unbelievable price!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Joe Cleary (941-650-8485)
6006 MIDNIGHT PASS RD #51, SARASOTA, FL 34242
$575,00054 Days on yellowkey MLS ID: P4938368
Bed: 1 Bath: 0.0 Liv Area Sq Ft: 600 Built: 1960 Tax: $3,999 (2025)Community: Casa MarSpa: NoApartment
Taxes:$3,999
Remarks: PRIVATE BEACHFRONT CONDO! Experience the ultimate Siesta Key lifestyle with this beautifully updated, TURNKEY FURNISHED 1-bedroom, 1-bath residence in the highly sought-after Casa Mar community, offering 300ft of GULF/OCEAN FRONT, WATERFRONT, WATER ACCESS to the world-famous Siesta Key Beach. This property is ALREADY GENERATING INCOME with a strong short term rental history, making it an exceptional investment opportunity or personal beach vacation retreat. Perfectly positioned within the complex and just steps from the pool, this bright and modern unit features a spacious layout with a welcoming foyer (found in only select units), a large bedroom with abundant closet space, and a versatile Florida room overlooking the courtyard and pool...ideal for relaxing, morning coffee, or hosting guests. Hurricane-rated windows and doors provide peace, quiet, and year-round comfort. Enjoy resort-style amenities including two pools (one heated), tennis and pickleball courts, shuffleboard, BBQ grilling areas, picnic spaces, and lush tropical landscaping, all within a no-road-to-cross beachfront setting. Recent community upgrades include a NEW ROOF, NEW SEAWALL, landscaping, and a secure gated entry for added privacy. Additional conveniences include covered parking just steps from your door, nearby laundry facilities, onsite management, and a private mailbox. This high-demand weekly rental property offers both immediate income and future upside, with OWNER FINANCING AVAILABLE for added flexibility. Located just minutes from dining, shopping, and Siesta Key Village, with trolley access right outside, this is a rare opportunity to own a piece of paradise that seamlessly blends income potential with effortless coastal living. Seller financing and private financing available. Do NOT WAIT, it will not last long!
Listing is courtesy of: HUT REALTY, LLC (407-559-2929)
Listing Agent: Daniel Hut (863-400-6090)
6512 MIDNIGHT PASS RD #504, SARASOTA, FL 34242
$2,495,000437 Days on yellowkey MLS ID: A4643532
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1991 Built: 2006 Tax: $20,738 (2024)Community: Crescent Siesta KeyCondo
Taxes:$20,738
Remarks: This rare and exceptional turnkey Siesta Key residence offers an unparalleled blend of space, style, and sweeping Gulf views. Spanning nearly 2,000 square feet, this 3-bedroom, 2.5-bath coastal retreat features two expansive terraces—one overlooking the serene elevated pool and spa area, and the other offering unobstructed sunset vistas across the Gulf. Each of the three bedrooms enjoys private balcony access via sliding glass doors, creating a seamless indoor-outdoor living experience. Designed with a modern coastal aesthetic, the interior features full-thickness bamboo flooring in the main living areas, premium custom cabinetry, and sleek quartz countertops. Soaring 11.5-foot ceilings and clerestory windows with remote-controlled shades enhance the home’s light-filled, airy ambiance. The gourmet kitchen is equipped with top-of-the-line GE appliances, bar-height seating, and a pass-through window that frames the Gulf beyond. The open-concept living and dining areas are ideal for entertaining or quiet reflection, anchored by a Gulf-facing terrace and thoughtfully appointed with a Stressless reclining sofa and captain’s chairs—all perfectly positioned to take in the view. The spacious primary suite offers high ceilings, expansive windows with Gulf views, and blackout draperies for restful nights. The spa-style bath includes a multi-head oversized shower, a large vanity with quartz countertops, a dedicated makeup area, and tile flooring. Two additional bedrooms are configured for comfort and versatility, including a dedicated office in the third bedroom with a Murphy bed. A host of upgrades includes a Schlage Smart Entry Lock, Arlo security camera system, hardwired mesh network for seamless connectivity, a deck-mounted hot water dispenser, and an 80-gallon hot water heater with recirculating system. Additional conveniences include two dedicated parking spaces located on the first floor under the building and an air-conditioned storage cage (#4) on the fifth floor. Crescent offers an elevated beachfront lifestyle with private, direct access to Crescent Beach. The community is meticulously maintained, with newly renovated pools—including an elevated second-floor spa and a completed beachside pool and hot tub—fresh exterior painting, new landscaping, and a host of upscale amenities including a fitness center, social room, upgraded security system, and onsite manager. Ideally situated just off Stickney Point Bridge, this residence offers effortless access to Sarasota’s renowned dining, shopping, and cultural attractions. With Siesta Beach just steps away—recently named the No. 1 beach in America by Tripadvisor—this property captures the essence of Gulf-front living, whether as a full-time home, luxurious getaway, or investment opportunity.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
4822 OCEAN BLVD #11E, SARASOTA, FL 34242
$419,00047 Days on yellowkey MLS ID: TB8498225
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 820 Built: 1973 Tax: $4,517 (2025)Community: Siesta TowersSpa: NoCondo
Taxes:$4,517
Remarks: 11th-floor Gulf views, Siesta Key Beach right down the road, and a price point that gives you real upside. This the kind of condo/value comination people hope for. The unit has modest finishes as it sits, but the real play here is the value. You get a front-row seat to the Gulf, a private balcony for sunsets every night, and the chance to update it the way you want without paying a premium for someone else’s remodel. This is a bright west-facing 1-bedroom in Siesta Towers, so the natural light and water views are the star of the show. Whether you want a full-time place, beach getaway, or investment hold, this one checks the box for location and long-term potential. Siesta Towers is a well-kept beachfront community with a community pool, covered parking assigned by seniority, updated lobby/amenities, and beautifully maintained grounds. The building completed its milestone inspection in 2024, major exterior repairs were done in 2023, the roof was replaced in 2018, and the association fully funds both mandatory structural reserves and general reserves. You are also right in the middle of what makes this area so desirable. Siesta Key Beach is close by, and Siesta Key Village is right there for dining, shopping, and nightlife. It is hard to beat this combination of views, location, and value on Siesta Key.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Nathan Shirk (585-356-2197)
1269 DOCKSIDE PL #115, SARASOTA, FL 34242
$825,000245 Days on yellowkey MLS ID: A4656792
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1217 Built: 1982 Tax: $6,667 (2024)Community: Harbour TowneSpa: YesCondo
Taxes:$6,667
Remarks: This spacious condo has easy access to Siesta Key Beach and a DEEDED 25-FOOT BOAT SLIP WITH A LIFT!! There is water and electric to the slip (#38). Yes, this is a rare opportunity to have both your boat and a nearby world-famous beach in a nicely laid out two-bedroom, two-bath turnkey furnished condo. The master bedroom has views of the harbor while the guest room has a peaceful garden view. This condo features tile flooring throughout with both HVAC and appliances that are only a couple of years old. The roof was replaced in November 2021, and the unit has a one-car garage with storage above as well as a dedicated parking space in front. In addition, this unit has one of the few private outdoor decks in the community. Harbour Towne offers fantastic amenities, including a clubhouse, heated pool, spa, and tennis/pickleball courts. Enjoy the village by day or evening for great dining, shopping and live music. A complimentary trolley runs by the complex on a regular schedule in season. This is a great place to live and play! Look no further, this is where your fun-filled life begins.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Mina Johnson (941-404-9347)
1701 SOUTHWOOD ST #1701, SARASOTA, FL 34231
$260,000201 Days on yellowkey MLS ID: A4671475
REDUCED by $5,000 (1.9%) on 03/31/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1164 Built: 1981Monthly Fee: $1,273 Tax: $3,371 (2024)Community: Baywood ColonySpa: NoCondo
Taxes:$3,371
Remarks: RECENT PRICE ADJUSTMENT - MOTIVATED SELLERS! Rare Opportunity in Prestigious West of the Trail - Welcome to an exceptional corner residence just steps from the Intracoastal Waterway, nestled within the highly desirable Baywood Colony Southwood community. This beautifully updated 2-bedroom, 2-bath end unit is filled with natural light, enhanced by an abundance of windows complemented with elegant plantation shutters throughout. The front screened lanai has been fully enclosed with sliding glass panels and additional plantation shutters, creating a stylish and versatile space ideal for year-round enjoyment. Inside, the home presents like a model, featuring a stunning open-concept kitchen with granite countertops, a generous breakfast bar, stainless steel appliances, and premium soft-close wood cabinetry accented by under-cabinet lighting. A washer and dryer are conveniently located inside the residence, and elegant tile flooring extends throughout. Major improvements provide peace of mind, including a new A/C system (2018), a roof replacement by the HOA (2019), and a recently re-plumbed building. This ground-floor unit offers the added convenience of a covered parking space directly behind the residence, along with a secondary private entry from the carport. Residents enjoy an exceptional Florida lifestyle with access to a heated saltwater pool, tennis and pickleball courts just steps away, and tranquil walks to the Baywood Colony fountain—perfect for taking in spectacular bayfront sunsets. With only 32 residences, the community offers a rare sense of privacy and boutique-style living. The location is unbeatable: just 2.2 miles from beach access with an easy bike ride, and within walking distance to Phillippi Estate Park—a picturesque 60-acre waterfront preserve offering kayaking, fishing, scenic trails, a playground, a weekly Wednesday farmers market, and a variety of community events including art fairs and concerts. This pet-friendly, maintenance-free community includes basic cable, exterior and grounds maintenance, roof and window coverage, and pest control—all included in the low monthly fee of $1,273. Best of all, the community is not age-restricted. Experience the perfect blend of comfort, convenience, and coastal elegance in this truly special Sarasota residence.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Jo James, Llc (941-928-3175)
546A BEACH RD #A544, SARASOTA, FL 34242
$1,980,000322 Days on yellowkey MLS ID: A4657651
0 Days Off yellowkey (back on 4/23/2026)
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2611 Built: 1981 Tax: $20,998 (2024)Community: Tiffany SandsTownhouse
Taxes:$20,998
Remarks: Under contract-accepting backup offers. Gulf-front luxury townhome with private beach access on Siesta Key! Soak in the breathtaking, unobstructed views of the Gulf and iconic Siesta Beach from every level of this three-story, turnkey-furnished townhouse-style condominium. Just a short distance from the sand in the intimate, nine-residence enclave of Tiffany Sands, this rare Siesta Key offers blends relaxed beachside living with elegant design and modern comforts. Spanning 2,611 square feet, this three-bedroom, 3.5-bath residence welcomes you with an open-concept main floor that seamlessly connects the kitchen, dining and living areas—all framed by floor-to-ceiling impact-rated sliding glass doors and panoramic Gulf vistas. The living room is anchored by a cozy wood-burning fireplace and enhanced by crown molding, recessed lighting and sleek ceramic tile flooring. Go onto the expansive Gulf-front balcony, an ideal setting for alfresco dining or sunset lounging. The kitchen is stylish and functional, featuring solid-surface countertops, stainless steel appliances, modern cabinetry with pullout shelving, under-cabinet lighting and a breakfast bar for casual meals. Upstairs, the spacious Gulf-front primary suite offers postcard-worthy views, a private balcony, sitting area, double closets and a luxurious en-suite bath with jetted soaking tub, double vanity, separate shower, bidet and two skylights. Two additional guest bedrooms—flexibly configured with a retractable dividing wall—are also on the third floor along with a full guest bath and a well-equipped laundry room. The oversized ground-floor bonus room opens via sliding glass doors to a covered patio just steps from your private beach path. A full bath with walk-in shower was stylishly updated in 2024, making this level ideal for guests, a home gym or media lounge. Additional highlights include a one-car attached garage with extra storage, newer water heater (2024), HVAC (2022), roof and skylights (2017), hurricane shutters and flexibility of 30-day minimum rentals. Just .4 miles from Siesta Village’s vibrant shops and dining, and Siesta Beach Park, this exceptional home delivers the ultimate island lifestyle—whether you’re seeking a serene personal retreat, a seasonal escape or a savvy investment property.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Mike Warm, Llc (941-525-2740)
1429 N LAKE SHORE DR, SARASOTA, FL 34231
$5,595,000171 Days on yellowkey MLS ID: A4674740
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 4545 Built: 2026 Tax: $9,862 (2025)Community: Oyster Bay EstatesSpa: YesSingle Family
Taxes:$9,862
Remarks: One or more photo(s) has been virtually staged. Experience luxury West-of-Trail living in Sarasota’s coveted Oyster Bay neighborhood. This newly built 2026 custom residence offers 5 bedrooms, 5 full and 2 half baths—all on one thoughtfully designed living level—featuring 4,545 sq. ft. under air and 5,689 sq. ft. total. Set on an impressive 130' x 150' corner lot (0.45 acres), the home is surrounded by a lush tropical oasis that provides exceptional privacy. A dramatic two-story foyer with 21’ ceilings and a steel-and-impact-glass entry door welcomes you inside. Engineered oak hardwood flooring, 10” baseboards, and sleek horizontal receptacles enhance the home’s modern architectural aesthetic. The expansive open-concept kitchen and great room are flooded with natural light from ten windows and four 20’ hurricane-impact glass sliders that open to the outdoor living space. The gourmet kitchen is a chef’s dream, offering an 8-seat center island, large walk-in pantry, quartz countertops, and premium appliances including a Bosch 36” natural gas/induction cooktop, 36” Thermador refrigerator column, 24” Thermador freezer column, 24” full-height Thermador wine cooler, Bosch dishwasher, and 30” Bosch oven/microwave combo. Retreat to the luxurious main suite featuring a Wetstyle tub with wood surround, marble accents, and slate and porcelain flooring. Additional highlights include level-5 smooth interior walls, 8’ solid-core and obscure-glass interior doors, a stunning 175-bottle wine room with marble wall and glass enclosure, Samsung pedestal washer & dryer, and an advanced alarm and exterior security lighting system. The outdoor living area is designed for year-round enjoyment with a summer kitchen equipped with a Blaze 42” gas grill, sink, and under-counter refrigerator. A 15’ x 28’ pool and spa with a custom waterfall feature, plus an outdoor shower, complete this private retreat. The property also offers an irrigation system and a spacious 3-car garage. An exceptional opportunity to own a brand-new, luxury single-level home in one of Sarasota’s most desirable West-of-Trail communities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
5770 MIDNIGHT PASS RD #C601, SARASOTA, FL 34242
$1,395,000180 Days on yellowkey MLS ID: A4674063
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1337 Built: 1980 Tax: $11,117 (2024)Community: Gulf & Bay ClubSpa: YesCondo
Taxes:$11,117
Remarks: An exquisite, fully updated, fully furnished 2 bedroom 2 bathroom beach oasis! Located in the heart of Siesta Key at the exclusive upscale Gulf & Bay Club. Featuring high end detailed finishes and interiors professionally crafted to perfection. This unit is in C Building with direct beach access just steps away from your front door. Enjoy breath taking sunsets from your personal balcony or head down to the private beach for an up close view of the #1 beach in the US. The sandy white powder stretches 800 feet across this pristine 32 acre meticulously cared for tropical community. You will be impressed with world class amenities offered at Gulf & Bay Club. Enjoy the comfort of 24 hour gated security, heated pools, a fitness center, dry saunas, hot tub, tennis courts, just to name a few. Multiple barbecues and tiki hut picnic areas are great for entertaining your guests. The amenities don’t stop there, the club house has a library, bar, pool table and TV's all for your enjoyment. Not to mention the electric car charging stations and on site car wash. You are moments away from Siesta Village to enjoy alfresco dining with live music, specialty shopping and more! Take a short trip to the mainland and discover theater, art and fine dining. This is the island resort lifestyle you have been looking for, don't let your chance of fine beach living slip away.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Sylvia Wilk (630-863-1825)
3631 SAN REMO TER, SARASOTA, FL 34239
$7,995,000210 Days on yellowkey MLS ID: A4669078
REDUCED by $250,000 (3.0%) on 04/22/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4705 Built: 2021Monthly Fee: $13 Tax: $68,556 (2025)Community: San Remo EstatesSpa: YesSingle Family
Taxes:$68,556
Elementary School: Southside Elementary
Remarks: Anchored in one of Sarasota’s most coveted deep water waterfront communities, 3631 San Remo Terrace presents a rare opportunity to own a modern luxury home with direct boating access in San Remo Estates, just moments from Siesta Key, Downtown Sarasota, and Southside Village. Completed in 2021 by award-winning designer Stephen Chung and enhanced with thoughtful 2025 upgrades, this coastal contemporary residence blends clean architectural lines with warm, natural finishes, ideal for buyers seeking newer construction, move-in-ready condition, and hurricane-resilient design in a prime location. Positioned on protected sailboat water with no fixed bridges, the property offers seamless access to Sarasota Bay and a short, unobstructed ride to the Gulf, making it perfectly suited for avid boaters. Spanning approximately 4,750 square feet under air, with nearly 3,000 additional square feet of outdoor living space, the home is designed around the indoor-outdoor lifestyle today’s luxury buyers prioritize. The open-concept layout is anchored by a chef’s kitchen featuring a sculptural marble island and Sub-Zero and Wolf appliances, flowing effortlessly into a great light-filled room with a stone fireplace, custom built-ins, and floor-to-ceiling glass sliders that open to expansive terraces. A temperature-controlled wine room with 1,800-bottle capacity adds a refined touch, while the dining space creates a striking architectural focal point. The primary suite offers true resort-style living, with private access to both a tranquil courtyard with spa and sauna and the waterfront pool terrace. Inside, a custom walk-in closet and spa-inspired bath reflect the level of finish expected in a luxury retreat. The second level features three additional bedrooms, a flexible gym or office, and a loft-style workspace, providing versatility for modern living. Outdoors, the illuminated saltwater pool with a glass wall, newly enhanced outdoor kitchen, and expansive entertaining areas create a private waterfront oasis. The deep-water dock is equipped with a 20,000-pound boat lift, dual jet ski lifts, and a floating dock, delivering a true boating lifestyle. Additional highlights include a three-car garage with a lift, epoxy flooring, and custom storage. A fully integrated smart home system, featuring programmable lighting and shades, whole-home audio, Apple TV integration, a generator, and high-speed WiFi, meets the expectations of today’s tech-forward buyer. Furniture is available separately to create a more turnkey concept. Located within San Remo Estates, the home offers a rare balance of privacy and central convenience. Just minutes from Siesta Key via the nearby North Bridge, beach access becomes part of everyday life. Set on a deep-water basin seconds from Sarasota Bay, the property provides protected docking with immediate access to open water and a short ride to the Gulf. Southside Village and Downtown Sarasota are both a quick drive away without the need to cross any bridges, offering boutique shopping, cafés, acclaimed dining, and a vibrant arts and cultural scene. Everyday conveniences, including top-rated schools, Sarasota Memorial Hospital, and key corridors like US-41 and I-75, are all within close reach. This is a location that seamlessly connects protected waterfront living with the very best of Sarasota.
5500 MERRIMAC DR, SARASOTA, FL 34231
$1,685,00089 Days on yellowkey MLS ID: A4684914
REDUCED by $85,000 (4.8%) on 04/17/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2790 Built: 1974 Tax: $6,537 (2025)Community: Phillippi Gardens 08Spa: YesSingle Family
Taxes:$6,537
Remarks: Live the Ultimate Florida Lifestyle in This Waterfront Paradise! Nestled in the heart of Phillippi Gardens, this extraordinary property offers the perfect blend of tranquility, luxury, and convenience. Set on an OVERSIZED .61-ACRE LOT WITH OVER 400 FEET OF PRIVATE WATER FRONTAGE. Along two serene waterways just off Phillippi Creek, this home is a true tropical oasis—peaceful and secluded, yet minutes from everything Sarasota has to offer. Inside, the residence showcases a flexible layout with FOUR SPACIOUS BEDROOMS, some easily adaptable for office, studio, or guest use, and FOUR FULL BATHROOMS making it ideal for hosting loved ones and guests. The interior has been thoughtfully updated from 2017 through 2024 blending modern comfort with timeless charm. Interior Highlights Include: An expansive great room with a DUAL-SIDED WOOD-BURNING FIREPLACE, a gourmet kitchen featuring stainless steel appliances, farmhouse sink and pot filler. Three bedrooms on the main level, including one en-suite, and a second-floor master suite with a PRIVATE BALCONY OFFERING BREATHTAKING SUNRISE AND SUNSET VIEWS. Step outside and feel like you're on vacation every day. The lush, tropical grounds are packed with resort-style amenities: Tiki hut with a full bar and grill, two fire pits, five-zone low-voltage night lighting creating a magical evening ambiance, heated pool and spa, boat lift, a new boathouse (2019) and new seawall (2023/2024). Additional Upgrades: Two new A/C units (2019), septic-to-sewer conversion (2018). Tucked away at the end of a quiet cul-de-sac, this home offers privacy without sacrificing accessibility. You're just a short bike ride to the Gulf beaches, near The Landings for shopping and dining, and minutes from downtown Sarasota’s vibrant arts and culture scene.
Listing Agent: Steve Abbe (941-400-3969)
7433 SUMMER CT, SARASOTA, FL 34231
$1,151,90044 Days on yellowkey MLS ID: TB8498580
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2883 Built: 2026Monthly Fee: $378 Tax: $11,872 (2026)Community: GranduraSpa: YesSingle Family
Taxes:$11,872
Elementary School: Wilkinson Elementary
Tax Year: 2026
Remarks: Pre-Construction. To be built. Under construction and slated for completion in August/September. Welcome to Grandura, a gated, maintenance-free boutique community in the heart of Sarasota, offering a rare blend of a highly desired location and new construction west of I-75. This Imperial floorplan offers 4 bedrooms, 3.5 baths, a spacious loft, and over 2,500 sq. ft. of thoughtfully designed living space—loaded with high-end upgrades throughout. From the moment you enter, you’ll notice the elevated finishes, including 10’ ceilings, 8’ interior doors and luxury vinyl plank flooring throughout the entire first floor, creating a clean, modern feel. The open-concept layout is centered around a designer kitchen featuring white cabinetry, quartz countertops, and KitchenAid appliances, flowing seamlessly into the café and gathering room—ideal for entertaining. Step outside to your covered lanai overlooking a private pool and spa, with outdoor kitchen plumbing already installed.
Listing is courtesy of: PULTE REALTY INC (561-206-1417)
Listing Agent: Dan Wenstrom (941-229-3395)
7444 SUMMER CT, SARASOTA, FL 34231
$1,058,00546 Days on yellowkey MLS ID: TB8498059
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2563 Built: 2026Monthly Fee: $378 Tax: $10,904 (2026)Community: GranduraSpa: YesSingle Family
Taxes:$10,904
Remarks: Under Construction. Under construction and slated for completion in August/September. Welcome to Grandura, a gated, maintenance-free boutique community in the heart of Sarasota, offering a rare blend of a highly desired location and new construction west of I-75. This Imperial floorplan offers 5 bedrooms, 3.5 baths, a spacious loft, and over 2,500 sq. ft. of thoughtfully designed living space—loaded with high-end upgrades throughout. From the moment you enter, you’ll notice the elevated finishes, including 10’ ceilings, 8’ interior doors and luxury vinyl plank flooring throughout the entire first floor, creating a clean, modern feel. The open-concept layout is centered around a designer kitchen featuring white cabinetry, quartz countertops, and KitchenAid appliances, flowing seamlessly into the café and gathering room—ideal for entertaining. Step outside to your covered lanai overlooking a private pool and spa, with outdoor kitchen plumbing already installed.
749 TROPICAL CIR, SARASOTA, FL 34242
$1,575,000177 Days on yellowkey MLS ID: A4673529
4 Days Off yellowkey (back on 4/21/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2598 Built: 1984Monthly Fee: $54 Tax: $15,011 (2025)Community: Siestas Bayside Bayside Club 01Single Family
Taxes:$15,011
Remarks: Under contract-accepting backup offers. A private tropical haven in the heart of Siesta Key, beautifully reimagined coastal retreat tucked away on nearly half an acre in one of Siesta Key’s most coveted neighborhoods. This stunning four-bedroom, two-and-a-half-bath pool home lives effortlessly, blending relaxed island living with thoughtful modern design, all just minutes from world-renowned Siesta Beach and the vibrant energy of Siesta Village. Completely transformed in 2023 by the former contractor-owner for his family, the residence showcases quality craftsmanship, contemporary finishes, and a warm, inviting aesthetic. Sunlight pours through impact-rated windows, highlighting open living spaces that flow seamlessly toward the outdoors. The expansive great room anchors the home and connects naturally to the newly staged interiors, creating an ideal environment for everyday living and entertaining. At the heart of the home, the chef’s kitchen is an absolute showpiece, featuring a striking reclaimed-oak island, open oak shelving, handmade tile, quartz surfaces, premium appliances, and exceptional storage including a full-height pantry wall. The design balances beauty and function with ease. The spacious primary suite offers serenity and privacy with a spa-inspired bath, while three additional bedrooms provide flexibility for guests, family, a home office, or creative space. A full interior laundry room, half-bath, and oversized two-car garage add convenience. Step outside to your own tropical oasis. A large, screened lanai opens to lush gardens, a newly renovated pool with updated equipment, and an expansive paver deck; perfect for relaxing in the sun or hosting gatherings under the palms. This exceptional property offers peace of mind with solid concrete block construction, no flood or hurricane damage, and a long list of upgrades, including new kitchen, baths, plumbing updates, air conditioning and ductwork, water heater, pool equipment, paver driveway, and more. Move-in ready, beautifully staged and ideally located, this is coastal living at its best. Enjoy quick access to Siesta Beach, the Village, boat launches, dining, and all that Sarasota offers.
Listing Agent: Judie Berger (941-928-3424)
2475 BAY ST, SARASOTA, FL 34237
$2,012,000112 Days on yellowkey MLS ID: A4676732
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2874 Built: 2024 Tax: $14,004 (2025)Community: Hudson ParkSingle Family
Taxes:$14,004
Elementary School: Alta Vista Elementary
Remarks: Experience refined modern living at 2475 Bay Street, a brand-new contemporary residence offering 2,874 square feet of thoughtfully designed space. Clean architectural lines and a striking façade set the tone, while inside, sun-filled interiors reveal soaring ceilings, expansive open-concept living areas, and walls of glass that create a seamless indoor-outdoor connection. The home is designed to feel both elevated and livable, with spaces that flow naturally for entertaining, relaxing, and everyday life. The home features four bedrooms and four bathrooms, including a main-level primary suite that offers split-plan privacy and direct access to the pool area. The primary bath includes a double vanity, walk-in shower, soaking tub, and spacious his-and-hers closets with built-in accessories. The chef’s kitchen is outfitted with Café appliances accented in gold, premium cabinetry, Calcutta quartz countertops throughout the home, and a dramatic waterfall island seating eight. An upstairs living area overlooks the main level and opens to a second-story balcony, while additional bedrooms feature en-suite baths for comfort and privacy. Additional highlights include a custom resort-style pool, fully fenced yard, covered lanai with a fully equipped outdoor kitchen, two-car garage, energy-efficient construction, paver driveway accommodating up to four vehicles, and a mudroom with direct access to the pantry. Ideally located in central Sarasota, this home offers a peaceful residential setting with quick access to downtown and the area’s top attractions. Enjoy nearby Main Street dining, boutique shopping, and cultural venues such as the Sarasota Opera House, Florida Studio Theatre, and McCurdy’s Comedy Theatre. Outdoor and lifestyle destinations include Bayfront Park and Marina, Marie Selby Botanical Gardens, Payne Park, St. Armands Circle, Sarasota Jungle Gardens, The John and Mable Ringling Museum of Art, and Mote Marine Aquarium. World-renowned beaches including Siesta Key, Lido Key, and Longboat Key are just minutes away, along with convenient access to Publix, Sarasota Memorial Hospital, top schools, and Sarasota-Bradenton International Airport. Schedule your private tour and experience the design, flow, and lifestyle of this unique Sarasota property before it slips away.
Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)
Listing Agent: Desiree Doggett (941-900-6380)
1760 ARLINGTON ST, SARASOTA, FL 34239
$2,150,000291 Days on yellowkey MLS ID: A4661996
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2745 Built: 2012 Tax: $21,270 (2024)Community: Nichols Sarasota HeightsSpa: NoSingle Family
Taxes:$21,270
Remarks: One or more photo(s) has been virtually staged. Ideally positioned in Sarasota’s desired West of Trail, this 2012 custom-built three-bedroom, four-bath home blends timeless architecture with modern comfort—just a short stroll to Southside Village’s boutiques and cafés, Selby Gardens, the bay front, and Sarasota Memorial Hospital. Set on a fully fenced, 1/3-acre lot in the sought-after Southside Elementary district, the property offers a private oasis with a sun-soaked southern-exposure backyard—ideal for all-day light on the pool and covered patio. Outdoor living shines with a heated pool featuring a sun shelf, fire pit, landscaped lawn, and inviting front and back porches designed for effortless entertaining. Inside, nearly 2,800 square feet unfolds with a wood-burning fireplace, tile and luxury vinyl plank flooring, and a flexible layout suited for today’s lifestyle including a den/office that can easily be used as a fourth bedroom. The oversized laundry/mudroom streamlines daily life, while the two-car garage with extra storage adds convenience. The spacious primary suite opens directly to the pool and features dual walk-in closets and bath with double vanities, a walk-in shower, and soaking tub. Built with quality in mind—including block construction and a durable metal roof—this home offers peace of mind and enduring value. A rare opportunity to own newer construction West of Trail with accessibility, abundant natural light, and room to live the Sarasota lifestyle to its fullest—just minutes from downtown.
Listing Agent: Katy Mcbrayer (941-400-2406)
251 SOUTHWINDS DR, SARASOTA, FL 34231
$149,500220 Days on yellowkey MLS ID: A4669553
REDUCED by $10,400 (6.5%) on 04/21/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 624 Built: 1963Monthly Fee: $195 Tax: $1,434 (2024)Community: South Winds Mhp Co-OpMobile Home
Taxes:$1,434
Remarks: Want to live near Siesta Key without breaking the bank? Here is your opportunity, in one of the most desirable 55+ co-op communities, South Winds! And for only $195/month for HOA fees, you get to enjoy maintenance free living in a friendly and active neighborhood with a heated pool, shuffleboard, bocce, pickleball, horseshoes, a putting green, library and recreation hall and more! The home features newly screened in lanai's on both sides, an attached storage shed and an oversized lot, one of the best in the entire community with green space in the front, a garden area in the back, and just a short distance to all amenities. The bathroom is also recently remodeled with granite counter, and a new walk in shower. AC new in 2020, and the home was re-piped in 2022. There is also a termite warranty and contract that conveys to the new owner! Here is your opportunity to live just 5 minutes to Siesta Key and 10 minutes to downtown Sarasota. Gulf Gate is also just 5 minutes away for amazing local restaurants and entertainment.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Adrian Mociran (941-302-8603)
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