Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
3619 PEMBROOK DR, SARASOTA, FL 34239
$585,00083 Days on yellowkey MLS ID: A4681591
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1625 Built: 1970Monthly Fee: $8 Tax: $3,937 (2025)Community: Village Green Club EstatesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,937
Elementary School: Wilkinson Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Must see this special home! You'll want to move in immediately! Clean, neat, meticulously maintained home in desirable South Gate area, and golfing community, under $600,000. Freshly painted exterior August 2025 with new exterior light fixtures. Barrel tile roof maintenance in 2024, new flat roof over lanai, valleys redone, all roof penetration reflashed, attic solar fan installed. New AC in 2020 with whole house duct cleaning and ultraviolet light installed for mold control, extra insulation added in attic at the same time. New hurricane impact/energy efficient windows installed 2023 with lifetime warranty that is transferable. Hurricane garage door with Lift Master remote. Relax and breathe easy in the security of this block home. Water heater 2yrs. old. New electrical panel 2015. New stove top 12/25. Plenty of room to entertain friends and family on large 1600ft lanai area with extra large pool that looks like a lagoon of beautiful blue water. Pool cage screens replaced 2019, pool motor replaced 2022 and upgraded to variable speed motor. Pool and lanai decking resurfaced 2023. A piece of paradise as your backyard oasis is landscaped for privacy. Huge hass avocado tree grown from seed on side of house with banana trees, and pineapple plants in front that are the sweetest. Wood plantation shutters at all windows. Updated master bath, new tile in kitchen. Herringbone patterned floor tile. Updated ceiling fans add to great atmosphere. Inside laundry room, don't have to go into garage. Freshly cleaned roof and pool cage 11/25/25. 20 minute drive to famous Siesta Beach. Can't find a home in Sarasota in this excellent shape at this price.
Listing is courtesy of: SARABAY REAL ESTATE INC (941-355-7696)
Listing Agent: Debra Kelly (941-993-9129)
6480 MIDNIGHT PASS RD #403, SARASOTA, FL 34242
$1,100,000195 Days on yellowkey MLS ID: C7516381
1 Days Off yellowkey (back on 4/19/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1265 Built: 1979 Tax: $9,359 (2025)Community: Siesta BreakersCondo
Taxes:$9,359
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Remarks: Under contract-accepting backup offers. Fabulous Siesta Beach Condo at the Siesta Breakers #403 — Where Paradise Meets Profit Some properties are nice. This one is life-changing. Welcome to Unit #403 at Siesta Breakers — a rare, true beachfront end-unit perched directly on Crescent Beach, one of the most celebrated stretches of coastline on the planet. This isn't just a condo. It's a front-row seat to the Gulf of Mexico, every single day. Siesta Key's world-famous quartz-crystal sand stays cool even in the Florida heat — and 340 linear feet of it belongs exclusively to you and your guests. Across 5.6 lush acres, this gated community delivers a resort lifestyle that most only dream about. Inside, everything is already perfect. Bright. Open. Elevated. The open-concept living space flows effortlessly from designer interiors to a private balcony where sweeping Gulf views and legendary Siesta Key sunsets steal the show — every evening, without fail. The primary suite is a true sanctuary: a generous walk-in closet, an updated bath, and serene water views to wake up to. The guest bedroom is smartly designed for comfort, making it ideal for family or high-paying renters alike. It's offered completely turnkey — furniture, décor, and everything in between. Walk in and start living. Or start earning. Speaking of earning, the numbers speak for themselves. Unit #403 consistently generates $85,000+ annually in rental income, is already booked weekly through July 2026, and plugs directly into Siesta Breakers' highly sought-after weekly rental program. This isn't speculative income potential — the bookings are already in place. The community matches the lifestyle. Heated resort-style pool with tropical landscaping, Lighted tennis & pickleball courts, Private clubhouse, Security Gated Entrance, Secure under-building parking, Steps to island dining, boutique shopping & the free Siesta Key Breeze Trolley. Why #403 is the one: ? Prime beachfront end-unit — panoramic Gulf, pool & sunset views ? 340 ft. of private beach on world-renowned Crescent Beach ? Turnkey furnished & rental-ready from day one ? $85,000+ proven annual rental income ? Bookings already in place through July 2026 ? Low-maintenance luxury in a treasured, gated community Whether you're seeking your forever escape, a luxury vacation retreat, or a high-performing investment — this is the rare opportunity where all three align perfectly. Siesta Breakers #403 isn't just a purchase. It's a decision you'll never regret. Showings are only available on Saturdays between 2pm-4pm. Property is rented weekly thru July 2026.
Listing is courtesy of: CHARLOTTE COUNTY PROPERTIES (941-655-8804)
Listing Agent: Leo Albanes (941-626-9000)
2100 MCCLELLAN PKWY, SARASOTA, FL 34239
$6,000,00041 Days on yellowkey MLS ID: A4685416
Bed: 5 Bath: 8.0 Gar: 3 Liv Area Sq Ft: 4765 Built: 2026 Tax: $14,834 (2025)Community: Mcclellan Park ResubSpa: YesSingle Family
Taxes:$14,834
Elementary School: Southside Elementary
Remarks: Pre-Construction. To be built. Construction in progress, and opportunity for customizations. Situated West of the Trail, this exceptional estate represents the pinnacle of luxury living in Sarasota. Developed by Pham Development, this residence is a masterpiece of innovative, forward-thinking design and flawless craftsmanship. This home is 4,765 square feet, with 5 bedrooms, 7 baths and 2 half baths. Inside, you'll discover an open floor plan that harmoniously blends expansive spaces with comfortable, luxurious living. The soaring, 18-foot vaulted ceilings and seamless transitions between the grand indoor living areas, multiple patios, wrap-around balconies, and lush outdoor grounds make this home ideal for intimate gatherings and larger events alike. The well-appointed kitchen features an open-concept layout, highlighted by a stunning quartz island with waterfall edges, under elegant pendant lighting. Custom cabinetry in a sleek, glossy finish complements the state-of-the-art stainless-steel appliances, which include a professional-grade gas range, double ovens, and a built-in espresso machine. A discreet entry leads to a spacious butler’s pantry, offering additional storage, a secondary sink, and a prep area - perfect for hosting large gatherings or keeping the main kitchen organized. The pantry also mirrors the kitchen’s custom cabinetry and countertops for a seamless design. Adjacent to the dining area, a glass-enclosed, temperature-controlled wine room adds both style and function, and is sure to beautifully showcase your wine collection with custom shelving and ambient lighting. The expansive primary bedroom features 14-foot vaulted ceilings and large windows that fill the room with natural light. Soft, neutral tones create a serene environment, while the en-suite bathroom offers a spa-like retreat with a freestanding soaking tub positioned beneath a large window. Dual sinks with quartz countertops and sleek fixtures provide ample space, and the frameless glass walk-in shower features multiple shower heads and exquisite tile work. For entertainment, the theater room is a dream come true, offering tiered seating with oversized leather recliners - each equipped with cup holders and personal charging stations. The ultra-high-definition projection screen spans an entire wall, ensuring an immersive viewing experience. Outside, the resort-style pool is the centerpiece of the backyard, complete with a built-in spa, waterfall, and ambient lighting. A natural stone deck, covered lanai dining area, and a fully equipped outdoor kitchen and bar provide the perfect setting for outdoor living. A cozy fire pit with seating offers a perfect gathering spot for evenings, while the lush landscaping - featuring vibrant flower beds, mature trees, and decorative water features - creates a tranquil and picturesque setting. This outdoor space seamlessly combines comfort, style, and functionality for an exceptional living experience. Positioned on a grand parcel of approximately 20,505 square feet, this home offers privacy and tranquility amidst beautifully landscaped grounds. Whether you’re seeking the excitement of downtown Sarasota or the natural beauty of the Gulf, experience the perfect blend of luxury, comfort, and convenience in this exceptional home in a fabulous location.
Listing is courtesy of: THE STUTZMAN REALTY GROUP, LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
1050 W PEPPERTREE LN #116B, SARASOTA, FL 34242
$669,00056 Days on yellowkey MLS ID: A4684958
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1083 Built: 1974 Tax: $5,344 (2025)Community: Peppertree Bay IvSpa: NoCondo
Taxes:$5,344
Remarks: Turnkey coastal living on Siesta Key. Beautifully renovated first-floor Gulf-side garden condominium in the highly sought-after Peppertree Bay Gulf-to-Bay community. This exceptional two-bedroom, two-bath residence has been thoughtfully updated throughout and is offered fully turnkey furnished, creating an effortless opportunity to arrive and immediately enjoy the island lifestyle. The bright end-unit layout features a rare windowed kitchen that fills the living space with natural light, a feature seldom found in comparable garden units. The residence has been extensively improved with brand-new hurricane-impact windows, new flooring throughout, and numerous major system upgrades, including a recently replaced HVAC system, hot water heater, and dishwasher, providing peace of mind and reducing future maintenance expenses for the next owner. In addition, there is expanded square footage, enhancing the overall functionality of the home. The enclosed lanai area overlooks a tranquil lagoon and fountain, offering a peaceful setting for morning coffee or evening relaxation. Additional conveniences include a private in-unit washer and dryer, a dedicated exterior storage room, and assigned parking just steps from the entrance. Peppertree Bay is one of Siesta Key’s most desirable waterfront communities, uniquely positioned Gulf-to-Bay and offering a full suite of resort-style amenities that support a true full-service coastal lifestyle. Residents enjoy private beach access with chairs, two heated swimming pools, tennis courts, pickleball courts, a fitness center, fishing pier, newly updated clubhouse, gas grills, and on-site management with rental services. Ideally located just minutes from Siesta Key Village’s restaurants, shopping, and the world-renowned quartz sand beaches, this beautifully updated residence offers a rare combination of turnkey convenience, meaningful capital improvements, expanded living space, and premier coastal location. While the current owners have chosen not to rent the property, Peppertree Bay’s on-site rental management and strong seasonal demand provide an excellent opportunity for owners who wish to generate rental income.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Renee Nadiv (941-299-4242)
5295 ASHTON PINES LN, SARASOTA, FL 34231
$445,00097 Days on yellowkey MLS ID: A4678123
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1495 Built: 1987 Tax: $4,212 (2025)Community: Ashton PinesSingle Family
Taxes:$4,212
Remarks: Welcome to Ashton Pines, a community of 11 homes conveniently located to everything Sarasota has to offer. The updates in this home are dramatic featuring an open floor plan with volume ceilings in the great room. The expansive kitchen has upgraded cabinets & appliances with marble(yes, MARBLE) counter tops. There is a spacious breakfast area. The expansive primary bedroom has volume ceilings and a large half round window for amazing natural light. In addition to a 7 x 5 walk in closet, there is an upgraded private bath. The oversize shower stall has 2 shower heads, one a rain shower. There is a private courtyard with a sliding glass door that brightens the whole room. The split plan has two bedrooms on the north side of the home along with the main bath. The kitchen, living room, & primary bedroom all have sliders to access the screened lanai and rear yard. The laundry room offers additional storage and access to the 2 car garage. The access to Siesta Beach(2 miles), I75(5 miles),and any shopping or restaurants on Clark Road & Tamiami Trail is available with a quick drive. This is a great location for a primary home, secondary home, or an investment property.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Larry Brzostek (941-993-3125)
1404 KENILWORTH ST, SARASOTA, FL 34231
$5,200,000105 Days on yellowkey MLS ID: A4672697
REDUCED by $450,000 (8.0%) on 04/06/2026
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 5428 Built: 2007Monthly Fee: $333 Tax: $52,740 (2024)Community: Oyster Bay LandingsSpa: YesSingle Family
Taxes:$52,740
Tax Year: 2024
Remarks: Privately positioned in gated Oyster Bay Landings with water views stretching down a short canal to Sarasota Bay, this stunning iconic masterpiece from world-renowned architect Guy Peterson is a breathtaking example of the Sarasota School of Architecture’s style and vision. A comfortable modernistic ambiance flows freely throughout the 5,428 sq. ft. of open living where walls of glass capture spectacular displays of the cerulean blue water and evening skies of fiery beauty. No detail has been overlooked. No expense has been spared. Architecturally striking, this 4-bedroom, 4.5-bath waterfront residence is the ultimate indulgence offering rarity, cachet and grandeur. Dock with 2 lifts is conveniently situated on a waterway unencumbered by any bridge. Floor to ceiling windows frame expansive vistas and abundant natural light complements the thoughtfully-appointed and expertly-planned space. Over 4,000 square feet of outdoor area is inviting and festive, and presents unique vantage points to deliver an exhilarating experience. Expansive terraces promote seamless indoor-outdoor living. Covered entertaining is abundant among the verdant tropical gardens and immaculately manicured grounds. Resort-style amenities including an elevator, courtyard with fire pit and heated pool/spa, and breathtaking reflecting pool with fountain. The stunning kitchen is a culinary delight and complemented by an extravagant amenities package of top-tier appliances, island with seating for 6, 20-ft. long counter for 2 desk workstations, side-by-side but separate refrigerator and freezer, 2 dishwashers, and deep walk-in pantry. The family room is equipped with built-in entertainment wall and opens to a waterfront patio with outdoor cooking center. The great room has travertine floors and cypress ceiling detail, and the office provides a desk with stone countertops and plenty of solid wood cabinetry. A 400-bottle wine room is the highlight of the gaming area with wet bar, electric shades and unique glass chandelier. On the second level are spa-inspired en-suite bedrooms with custom closet systems and elevated ceilings. A 30-ft. bridge leads to the master wing highlighted by incredible water views, sitting room with morning bar, and home gym/office. The primary bath creates an immersive experience with a 16-ft. long dressing hall with a wall of built-ins and mirrors, large walk-in specialty closet, multi-faceted shower, deep soaker Jacuzzi tub, separate bidet and laundry chute. In addition, there are two laundry areas, an elevator from ground level to the 2nd and 3rd floors, Creston music and lighting system, Generac generator, and 4-car garage. In one of Sarasota’s most coveted locations along the waterfront, this home redefines coastal living is just minutes from beaches, golf, fine dining and downtown Sarasota’s beloved arts and cultural offerings. When scheduling your exclusive tour of this amazing MODERN waterfront estate, make sure to allow plenty of time for exploring its incredible features, both inside and out. It must be seen in person to be fully appreciated. Even the most discerning buyer will fall in love!
Listing is courtesy of: GRECO REAL ESTATE (941-685-0449)
Listing Agent: Karen Greco (941-504-6927)
5880 MIDNIGHT PASS RD #206, SARASOTA, FL 34242
$1,335,000195 Days on yellowkey MLS ID: A4668223
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1642 Built: 1982 Tax: $10,871 (2025)Community: CasarinaCondo
Taxes:$10,871
Remarks: Find your beach get-away in this remodeled three-bedroom Casarina condo located on Siesta Key’s famous Crescent Beach. This stunning TURNKEY FURNISHED and updated unit includes an open concept kitchen with high-end custom soft-close cabinetry, designer hardware and granite countertops. The great room was extended to incorporate the balcony into the living space creating an open and airy feeling to this home. A wall mounted television with Sonos audio provides family entertainment. The spacious primary bedroom with a Closet Tech designed walk-in closet opens to a large bathroom with custom cabinets, dual sinks and large walk-in shower. A third bedroom was created during the recent remodel and includes a built-in under window desk. The full-sized laundry room allows for plenty of storage. Luxury vinyl flooring was installed in 2020 in all public rooms. Impact windows were added in 2016. Electric blinds can close off the sliding glass doors to the outside view while all other windows have custom designed plantation shutters. Crown molding and solid wood doors are found throughout the unit. Casarina is an 89-unit condominium complex that sits on 200 feet of private beach and encompasses 7 acres of tropical landscaping. The complex has a clubhouse with kitchen. Spend your days enjoying the beachside pool and spa, play a game of pickleball on one of the two lighted tennis courts, or relax on the island’s famous crystal sand beach. Hop on the free trolley to enjoy the dining, shopping and entertainment at Siesta Key Village. CASARINA ALLOWS OWNERS ONE SMALL PET.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Suki Scollo (941-587-2289)
5880 MIDNIGHT PASS RD #306, SARASOTA, FL 34242
$1,285,000221 Days on yellowkey MLS ID: A4665591
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1498 Built: 1982 Tax: $8,594 (2025)Community: CasarinaCondo
Taxes:$8,594
Remarks: Welcome to Your Siesta Key Sanctuary. Step into paradise with this turnkey furnished condo in the highly sought-after Casarina complex, offering 200 feet of private beach access on the world-renowned Crescent Beach. Nestled on a lush 7-acre property, Casarina features beautifully landscaped gardens, tennis and pickleball courts, a beachside pool and spa, an elevated beach deck, and a welcoming clubhouse—all just steps from the famous crystal sands of Siesta Key Beach. Located on the third floor, this residence boasts a newly updated kitchen, luxury vinyl flooring, an updated guest bath, and a new AC unit. Enjoy serene garden views from your 17-foot screened balcony, with a peek-a-boo view of the Gulf and pool areas. Need extra space? The flexible 8’ x 8’ breakfast nook can easily be transformed into a home office or additional sleeping area. Casarina is a well-maintained 89-unit complex with fully funded reserves and recent complex renovations. Owners can bring one small pet, and enjoy the convenience of a covered carport and access to the free Siesta Key Trolley for dining, shopping, and entertainment. Whether you're paddle boarding, kayaking, biking, or simply relaxing on the beach, this condo offers the perfect blend of island lifestyle and resort-style amenities.
1473 LANDINGS CIR #44, SARASOTA, FL 34231
$468,888253 Days on yellowkey MLS ID: A4662144
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2040 Built: 1981 Tax: $6,233 (2024)Community: Landings TreehouseCondo
Taxes:$6,233
Remarks: Welcome to The Landings Treehouse, one of Sarasota’s most sought-after gated communities. This spacious 3-bedroom, 2.5-bath residence offers over 2,000 sq. ft. of living space with a thoughtfully designed open floor plan that balances comfort and style. The main level features a bright living and dining area with soaring ceilings, skylights, a cozy fireplace, and access to a private lanai surrounded by lush tropical landscaping. The updated kitchen boasts granite counters, a center island, breakfast bar, solid wood cabinetry, and stainless-steel appliances—perfect for both everyday living and entertaining. Upstairs, the primary suite offers a walk-in closet, high ceilings, and a spa-inspired bathroom with skylights that fill the space with natural light. Two additional bedrooms provide plenty of room for guests, one with its own en suite bath. Throughout the home, you’ll find luxury vinyl and tile flooring, designer finishes, and built-in features that enhance functionality. Set among mature trees and serene nature, The Landings Treehouse community is known for its exclusive amenities, including a heated community pool, tennis courts, walking trails, and private access to the Intracoastal Waterway through the Landings Racquet Club (membership optional). This desirable location places you just minutes from Siesta Key Beach, Downtown Sarasota, St. Armands Circle, and a variety of shopping, dining, and cultural attractions. With its generous floor plan, resort-style amenities, and unbeatable location, this home is the perfect opportunity to enjoy the relaxed yet vibrant Sarasota lifestyle.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Lisa Michel (941-702-3889)
2303 LOMA LINDA ST, SARASOTA, FL 34239
$1,899,000122 Days on yellowkey MLS ID: A4676235
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2708 Built: 2025 Tax: $4,955 (2025)Community: Loma Linda ParkSpa: NoSingle Family
Taxes:$4,955
Elementary School: Alta Vista Elementary
Remarks: Fantastic $100,000 price reduction!!! In the well-established Loma Linda Park neighborhood in Sarasota, this new construction, Divald Homes custom-built two-story home offers a blend of modern design and traditional elements. The home is ideally near downtown Sarasota, Siesta Key and Sarasota Memorial Hospital, with no deed restrictions or HOA fees. The home features four bedrooms and three baths, including a spacious primary suite on the main floor. The open-concept floor plan featuring a 24-by-48-inch modern floor tile throughout, hurricane impact sliding doors and windows offers a light-filled welcoming space ideal for entertaining. The main floor includes a gourmet kitchen, dining area, living room, private den/bedroom 4, primary suite with an ensuite bath and a dedicated laundry room. The chef’s kitchen is a centerpiece, showcasing Bosch appliances, an oversized island with waterfall quartz countertop, and custom floor-to-ceiling full-overlay cabinetry in a beautiful honey-stained wood tone. The living room is highlighted by a striking tile accent wall with custom wood shelving and modern designed 42-inch linear electric fireplace. The living room opens seamlessly to the lanai, complete with an outdoor kitchen, including a gas grill, refrigerator and sink. You will also enjoy the pool with sundeck, oversized outdoor patio and a beautiful backyard with lush native plantings. A convenient pool bath offers direct access from the lanai and the private den. The dining area is elegant and inviting, featuring a statement iron chandelier and a wall of windows overlooking the backyard. Just off the kitchen, the main-floor primary suite serves as a private retreat with a luxurious en-suite bath featuring a marble stone accent wall, a large walk-in shower with seamless glass enclosure, a sculptural slipper tub, double vanity with quartz countertops, natural wood cabinetry, LED mirrors and a spacious walk-in closet with custom built-ins. The laundry room is conveniently near the oversized two-car garage with 12-foot ceilings, large windows for natural light and direct access to the side yard. Upstairs, an ornate wrought-iron and hardwood staircase leads to two additional bedrooms, a beautifully finished guest bath and a versatile flex room ideal for a game room, study or guest accommodations. This thoughtfully designed home offers refined finishes, flexible living spaces and an exceptional location, ideal for enjoying the Sarasota lifestyle.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Robert Sherman (941-313-1301)
1169 W PEPPERTREE DR #118A, SARASOTA, FL 34242
$649,00058 Days on yellowkey MLS ID: A4683913
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1083 Built: 1974 Tax: $4,521 (2025)Community: Peppertree Bay IiiCondo
Taxes:$4,521
Remarks: Discover this impeccable, light-filled second-floor End unit in Peppertree Bay, offering serene views of the tranquil pond. Meticulously remodeled and lovingly maintained over 20 years, this residence exudes pride of ownership. Featuring two bedrooms and two bathrooms, the unit is complete with impact windows throughout, ensuring safety and comfort. Every square inch of this home has been tastefully enhanced, and the furnishings are included for your convenience. Enjoy the added convenience of an in-unit washer and dryer. Residents of Peppertree Bay benefit from a wealth of resort-style amenities, including a private beach with lounge chairs, two heated swimming pools, a fitness center, saunas, tennis and pickleball courts, barbecue grills, a fishing pier, and dedicated on-site management. Ideally located just a short stroll from Siesta Village’s shops and dining, and a quick drive to Sarasota’s cultural attractions, this property embodies coastal living at its best. Whether you’re seeking a full-time residence, a winter retreat, or an investment opportunity with rental income potential, this exceptional beachfront property meets all your needs. Don’t miss your chance to embrace the Siesta Key lifestyle—where every day feels like a vacation.
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Brian Ward (941-650-7721)
1792 FLOYD ST, SARASOTA, FL 34239
$1,250,00062 Days on yellowkey MLS ID: A4684245
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2015 Built: 1951Monthly Fee: $2 Tax: $13,700 (2025)Community: Hudson Bayou/Midwood ManorSpa: YesSingle Family
Taxes:$13,700
Remarks: One or more photo(s) has been virtually staged. Great price for walled-in pool home in PRIME WEST OF TRAIL location, just a few blocks to Southside Village popular shops and restaurants and 1 block to Sarasota Memorial Hospital. The home was remodeled in 1996 and 2000 with vaulted ceilings, newer bathrooms and kitchen, split bedroom floor plan, pool (built in 2003 and Pebbletec resurfacing in 2026), interior laundry room and 1 car garage. Tile or wood floors throughout. Property re-piped in 2024, a/c 2019. Perfect for your residence or an easy investment property with weekly or monthly rentals allowed. Rental estimates range from $6k - 7.5k monthly depending on annual or weekly rental. Very limited rental availability in the area.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Barbara May (404-822-9264)
1958 MORRIS ST, SARASOTA, FL 34239
$1,195,000113 Days on yellowkey MLS ID: A4677121
REDUCED by $100,000 (7.7%) on 04/03/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2362 Built: 1957 Tax: $7,088 (2025)Community: HartsdaleSpa: YesSingle Family
Taxes:$7,088
Remarks: One or more photo(s) has been virtually staged. Now offering buyer incentives and priced below appraised value! This exceptional single-family pool home offers the perfect blend of space, flexibility, and prime Sarasota location. Featuring 4 bedrooms and 3 full bathrooms, this residence is thoughtfully designed to accommodate a variety of living arrangements, including two primary suites, each with its own en suite bathroom—ideal for multigenerational living, extended guests, or a private home office retreat. Light-filled living spaces flow effortlessly, creating an inviting atmosphere for both everyday living and entertaining. The functional layout offers privacy where you want it and openness where it matters most, making the home equally suited for relaxed coastal living or hosting family and friends. NEW ROOF 2025. NO STORM DAMAGE. Step outside to your private fenced backyard oasis, where an oversized sparkling swimming pool takes center stage—perfect for year-round enjoyment in Florida’s sunshine. Located West of the Trail, this home places you in one of Sarasota’s most desirable areas. Enjoy the convenience of being just minutes from Downtown Sarasota, with its vibrant arts scene, dining, and waterfront attractions. The popular Morton's Market and Hillview shops and restaurants are close by for everyday errands and casual nights out, "A" rated Southside Elementary School just around the corner, Siesta Key Beach and Sarasota Memorial Hospital are only moments away, adding peace of mind and unmatched accessibility. Whether you’re searching for a full-time residence, seasonal getaway, or smart investment, this home stands out with its versatile floor plan, unbeatable location, and outstanding value. Opportunities like this in such a sought-after Sarasota setting—are rare. Schedule your private showing today and experience the lifestyle this property has to offer.
Listing is courtesy of: WAGNER REALTY (941-955-1500)
Listing Agent: Jon Patella (941-228-1613)
1690 ASSISI DR #12, SARASOTA, FL 34231
$1,779,00014 Days on yellowkey MLS ID: A4690125
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3097 Built: 2007Monthly Fee: $388 Tax: $15,103 (2025)Community: Portofino On The BaySingle Family
Taxes:$15,103
Elementary School: Gulf Gate Elementary
Remarks: Don’t miss this stunning Mediterranean-Tuscan-style residence, perfectly situated just steps from the Intercostal. This gated Sarasota estate home located in Portofino on the Bay includes its own DEEDED boat slip and remote controlled 10,000 LB. boat lift. Experience being near waterfront without the need for any flood insurance or stress of flooding, but still have your boat in your backyard with Bay access. This model-home-ready property features a private feeder dock slip, offering effortless access to the open water for boating. The Bay opens almost directly across from the newly opened midnight pass with Caribbean worthy turquoise water. Inside, the home has been completely renovated with top-of-the-line appliances and designer finishes throughout, blending luxury with comfort in every detail. The luxury chefs kitchen was renovated in 2023 leaving nothing out, complete with Fulgor Milano appliances. Enjoy the convenience of a first floor master with en suite and his and her wardrobes, a large home office and 10 foot-high ceilings with arched entryways throughout and a 25 foot high foyer with impressive feature wall and fireplace. The upstairs features impressive Cumaru wood flooring and stairs, three large bedrooms and a newly renovated bathroom with tub. The guest suite shows off with a Juliet balcony overlooking the private back yard. The open and inviting layout flows seamlessly into a serene private courtyard - perfect for relaxing or entertaining guests. Unwind in the soaking spa and enjoy the convenience of being just a short drive to downtown Sarasota, world-famous Siesta Key Beach, The Legacy Trail and the newly developing Sarasota Square, placing shopping, dining, and entertainment right at your doorstep. The Portofino on the Bay community has a Kayak Launch, kayak storage and a guest slip for daily visitors passing through. This exceptional home combines timeless architecture with modern elegance in a prime near waterfront location. Don’t miss out on this one.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Alexandra Lawson-Baker (703-963-4887)
2806 UPPER TANGELO DR, SARASOTA, FL 34239
$499,00034 Days on yellowkey MLS ID: A4687698
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1538 Built: 1958Monthly Fee: $17 Tax: $4,501 (2025)Community: South GateSingle Family
Taxes:$4,501
Remarks: Welcome to this beautifully updated 3-bedroom, 2-bathroom home in the highly sought-after South Gate neighborhood of Sarasota, ideally located just minutes from world-famous Siesta Key Beach and vibrant Downtown Sarasota. Situated on a highly desirable corner lot, this move-in ready home offers exceptional curb appeal with a newly installed 8-ft vinyl fence, along with a new roof, fascia, and gutters completed in 2023. Step inside to an inviting, light-filled living space where large windows create a bright and airy atmosphere. The flexible layout flows seamlessly into a versatile bonus area—perfect for a home office, sitting room, or additional entertaining space. The updated eat-in kitchen is the heart of the home, featuring freshly painted cabinetry, quartz countertops, stainless steel appliances, and a stylish backsplash—designed for both everyday living and hosting. A dedicated laundry room with built-in shelving doubles as a convenient pantry for added storage, and the home includes a new washer and dryer. French doors lead to the screened lanai, with upgraded wood tile flooring, creating a warm and inviting outdoor living space perfect for relaxing or entertaining. The fully fenced yard, mature canopy, and producing lychee tree contribute to a setting that feels both established and quietly distinctive. This backyard also offers room for play and possibly a pool for the future owner. The primary suite offers a peaceful retreat with an updated ensuite bathroom, featuring a new vanity and walk-in shower. Additional upgrades include fresh interior and exterior paint, new landscaping, vinyl flooring throughout, and added attic insulation (2024) for improved energy efficiency. This home is equipped with hurricane shutters, a 360-degree security system, and surge protection in the electrical panel for added protection and peace of mind. Furniture is available for purchase separately, making this a potential turnkey opportunity. Residents have the option to join the voluntary HOA, which provides access to the South Gate Community Association pool—an added perk that enhances the neighborhood lifestyle. Enjoy an unbeatable Sarasota lifestyle just minutes from shopping, dining, and entertainment, with easy access to the Legacy Trail, Siesta Key and St. Armands Circle. Whether you're searching for a primary residence, seasonal retreat, or investment property, this South Gate home offers the perfect blend of location, upgrades, and lifestyle. The property is maintained with consistent professional care, supporting long-term integrity. Schedule your private viewing today!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Roni-Marie Gold, Pa (941-487-0105)
35 SANDY COVE RD #2A, SARASOTA, FL 34242
$975,000212 Days on yellowkey MLS ID: A4653716
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1254 Built: 1970 Tax: $7,373 (2025)Community: Sandy CoveCondo
Taxes:$7,373
Remarks: Sandy Cove – Mid-Century Modern Gulf Front Paradise: Period-preserved mid-century architecture meets breathtaking Gulf front water views in this exceptional Siesta Key residence. Located in Sandy Cove, a hidden gem and distinguished 1970s development of villas and mid-rises, this fifth-floor residence offers a panoramic vista over Big Pass to Lido, Bird Key, and downtown Sarasota—a guaranteed "wow" moment. Sandy Cove Condos was designed in 1969 by Frank Folsom Smith with James Holliday and James Durden, earning a 1970 AIA Florida Award for architectural excellence. This light-filled, architecturally preserved residence is over 1,200 square feet with two bedrooms, two bathrooms, and a thoughtful split floor plan. Upon arrival, you're greeted by a charming garden courtyard that offers a glimpse into the home. Step inside and be captivated by the spectacular living room featuring soaring vaulted ceilings that provide ample natural light and an airy, open ambiance. Enjoy breathtaking Gulf water views from your living room and kitchen sliders, which open seamlessly to your private patio. The sliders pull back to welcome Gulf breezes throughout the entire residence, connecting to several delightful porches and patios—including an additional private palm tree patio with IPE decking. A rare and highly coveted feature: this residence includes a private one-car garage. Gulf front residences in Sandy Cove rarely become available, making this a unique chance to own a piece of Siesta Key's architectural history. The home has potential to be sold furnished and is offered in as-is condition, presenting an opportunity for buyers to customize their personal vision. Ideally situated close to Siesta Key Village—just a short distance away, this truly unique location offers a natural private beach exclusive to the community, along with a fishing pier. Come see this truly "if you know, you know" treasure on Siesta Key.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Mickey Kiernan (941-402-9115)
1055 W PEPPERTREE DR #102AA, SARASOTA, FL 34242
$850,000107 Days on yellowkey MLS ID: A4677695
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1163 Built: 1974 Tax: $4,365 (2025)Community: Peppertree Bay IvSpa: YesCondo
Taxes:$4,365
Remarks: Rare opportunity to own one of the most resilient and desirable residences on Siesta Key! This 2-bedroom, 2-bath condominium offers 1,163 square feet of living space (1,462 gross square feet) and is ideally positioned on the west side of the building on an elevated first floor, approximately 15 feet above sea level. It is also the closest high-rise condominium to the beach, offering exceptional proximity to the Gulf. One of only six residences in the building with an expansive deck, this sought-after middle-unit location provides a truly rare outdoor living experience. The oversized deck offers ample space for dining, entertaining, or simply relaxing while enjoying coastal breezes and sunsets. The residence has demonstrated remarkable storm resilience, sustaining no damage through three major hurricanes. This is attributed to its elevated positioning, protected west-side exposure, and six hurricane-rated doors installed in 2021. Recent interior upgrades enhance both style and comfort, including luxury vinyl flooring and freshly painted walls completed in 2025. The refrigerator, washer, dryer, and garbage disposal were also replaced in 2025. A dedicated parking space conveys with the unit. Owned by the same family since 1976, the home reflects decades of pride of ownership and thoughtful care. The community features two pools and two clubhouses on both the Gulfside and Bayside, along with a Gulfside fitness center. A well-managed rental program offers flexibility for owners while preserving a relaxed residential atmosphere. Located in one of Florida’s most coveted coastal settings, this exceptional residence offers a rare blend of scarcity, storm resilience, expansive outdoor living, and resort-style amenities—making it an outstanding lifestyle choice and investment opportunity.
Listing is courtesy of: REALTY HUB (407-900-1001)
Listing Agent: Tanya Stutzman (941-504-8785)
6725 ROXBURY DR, SARASOTA, FL 34231
$439,00078 Days on yellowkey MLS ID: A4682016
REDUCED by $10,900 (2.4%) on 04/15/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1718 Built: 1970Monthly Fee: $6 Tax: $5,286 (2025)Community: Gulf GateSingle Family
Taxes:$5,286
Remarks: This beautifully updated Gulf Gate residence is a true standout, offering the perfect blend of comfort, style, and high-impact upgrades. Plus, enjoy a 1% lender credit at closing. Step inside to a bright, open layout enhanced by crown molding, modern coastal lighting, and a fully remodeled kitchen designed for both everyday living and entertaining. The kitchen features granite countertops, upgraded stainless LG appliances (2022–2023), an induction range, convection microwave with air-fry capability, oversized refrigerator, and bar-height seating that keeps you connected with guests. Major system upgrades provide exceptional peace of mind, including a brand-new roof (2024), new electrical panel (2021) with generator transfer switch, whole-house surge protection, EV charging outlet, hot water heater (2020), upgraded R25 attic insulation, and a smart attic fan. A new 2025 HVAC system with UV light enhances air quality and efficiency, while split AC units (2023) in the family room and third bedroom offer flexible climate control. Both bathrooms have been tastefully updated with granite countertops, and additional features like a storm-rated garage door, clear storm shutters, Ring doorbell, and tri-fuel generator add an extra layer of security and convenience. The garage is thoughtfully equipped with built-in cabinetry, a laundry sink, and motion-sensor lighting. Enjoy Florida living at its best with a spacious fenced backyard and paver patio, perfect for relaxing or entertaining. Located in deed-restricted Gulf Gate, residents enjoy sidewalks, streetlights, and close proximity to shopping, dining, and the local library. You’re just minutes from Gulf Gate Village, Siesta Key Beach, Legacy Trail, top-rated schools, fitness centers, and the vibrant arts and theater scene of downtown Sarasota. This is a move-in-ready home where the big-ticket items are already done — schedule your private showing today.
Listing is courtesy of: EXP REALTY, LLC (941-462-3321)
Listing Agent: Jennifer Kenna (941-253-3003)
2156 ORCHID ST, SARASOTA, FL 34239
$950,000246 Days on yellowkey MLS ID: A4663262
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1850 Built: 2024 Tax: $3,119 (2024)Community: South GateSpa: YesSingle Family
Taxes:$3,119
Remarks: If you’re looking for a true “wow” factor, this stunning new-construction residence delivers. This custom-designed home combines luxury finishes with thoughtful functionality. Step inside to soaring 16-foot ceilings and dramatic exposed beams in the great room, creating an impressive sense of space. The chef’s kitchen is the centerpiece, featuring a striking brown agate back-lit island, Mustang granite countertops, modern cabinetry with pullouts and utensil organizers, an eight-burner professional range with bread and baking oven, custom vent hood, and upscale appliances—perfect for entertaining. Throughout the home, you’ll find large-format tile floors, custom window treatments, and the option to purchase designer furnishings. Offering 3 spacious bedrooms and 2.5 baths, this residence blends style and comfort seamlessly. Outdoor living is just as impressive, with a brand-new modern pool and pool cage (completed August 2024), a Jacuzzi brand hot tub, and a private outdoor shower with hot and cold water. The property is professionally landscaped, freshly painted inside and out (August 2025), and boasts impact windows and doors, ensuring safety, efficiency, and some of the lowest homeowners insurance rates available. Additional highlights include a tankless gas water heater, gas and electric dryer connections, and no flood zone location. Situated on one of Sarasota’s highly coveted “Flower Streets,” this property offers rare flexibility: the City of Sarasota permits 7-night minimum rentals, and the home is not subject to Southgate deed restrictions. Just 1 mile south of Sarasota’s luxury waterfront downtown, and less than 3 miles to the world-famous Siesta Key Beach, the home is also walkable to Conner’s Steakhouse, Baker & Wife, shopping, dining, banks, and groceries—all tucked away on a quiet dead-end street. Make an offer
Listing is courtesy of: CLUB REALTY (941-726-2677)
Listing Agent: Brooke O'Malley (941-726-2677)
1160 WAGON WHEEL DR, SARASOTA, FL 34240
$1,600,000146 Days on yellowkey MLS ID: A4673997
REDUCED by $100,000 (5.9%) on 04/18/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2467 Built: 1976 Tax: $5,221 (2024)Community: Fox Creek AcresSingle Family
Taxes:$5,221
Remarks: Welcome to a private 5 acre luxury estate, a rare multi residence retreat in the heart of Sarasota. Tucked behind a picturesque canopy of mature oaks and white ranch fencing, this exceptional property offers unmatched space, serenity, and versatility, featuring a beautifully maintained main residence, a fully equipped two story barn home with both upstairs and downstairs living accommodations, a sparkling saltwater pool, and acres of cleared usable land. The main home offers 3 bedrooms plus a large game room with a full closet that can serve as a fourth bedroom, office, or flex space depending on the buyer’s needs, along with multiple living areas and wide open spaces filled with natural light and peaceful views of the pool and surrounding acreage. Meaningful updates include appliances replaced in 2024, a whole house water softener system in 2024 including the apartment, septic pumped in 2024 with a new leech bed installed for both the home and apartment, a saltwater pool pump replaced in 2024, AC replaced in 2020, water heater replaced in 2019, and a durable metal roof from 2008. The expansive kitchen opens to the pool and living areas, complemented by a beautiful stone fireplace and a large bonus room perfect for a billiards room, playroom, gym, or hobby space. Outdoor living shines with a fenced saltwater pool and paver deck, ideal for sunny afternoons and relaxed evenings under the mature oak trees. The two story barn home is divided into two separate units, offering incredible flexibility for multigenerational living or rental income. The upstairs unit features 2 bedrooms and 1 and a half bathrooms, along with 2015 appliances and a private screened balcony overlooking the property. The downstairs unit includes 1 bedroom and 1 bathroom, updated flooring, granite counters, a 2020 stove and dishwasher, and a 2022 refrigerator. The barn also features a metal roof from 2006 and benefits from the recent septic upgrades. The full 5 acres are fully fenced and usable, perfect for horses, gardens, recreational vehicles, or future expansion, all accessed by a beautiful winding paved driveway and an oversized three car garage. This property offers peaceful privacy while still being close to shopping, dining, medical facilities, parks, I 75, and just a short drive to Siesta Key, Lido Key, and the world renowned Gulf Coast beaches.
Listing Agent: Katie Cobb (913-744-0248)
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