Location: Sarasota
Keyword(s): Sarasota High
Keyword(s) High School: Sarasota High
Do Not Show Listings
1541 FLOWER DR, SARASOTA, FL 34239
$1,870,000397 Days on yellowkey MLS ID: A4656365
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3302 Built: 1956 Tax: $7,456 (2024)Community: Harbor AcresSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,456
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2024
Middle School: Brookside Middle
Remarks: This unique home is in the desirable neighborhood of Harbor Acres. World renowned Selby Botanical Gardens is less than a mile from your new home. This mid-century jewel was built in 1956 and was originally a 2/2. The original bathrooms are still in their original state and are in good condition providing a cool retro vibe. The original hardwood floors and fireplace exude warmth and sophisticated charm. The current owner purchased the home in 1989 and remodeled the kitchen and added a new wing on the house with 2 additional large bedrooms ensuite with baths. Copious amounts of storage in all 4 bedrooms and a huge laundry room with lots of closet space as well. The garage is oversize and there is a picturesque circular driveway for ample parking. There is plenty of room to put in a pool of your own design. The house was re-roofed in 2018. Some of the most beautiful homes in Sarasota are your neighbors in Harbor Acres. And Flower Drive is a special address with the highly sought after Southside Elementary School just 1-mile away, you can’t beat this property. In real estate it is all about Location, Location, Location. This home has plenty of room for the family, so, come on home!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Kathleen Griffin (941-302-3979)
2304 SEATTLE SLEW DR, SARASOTA, FL 34240
$595,000188 Days on yellowkey MLS ID: A4678513
0 Days Off yellowkey (back on 6/10/2026)
REDUCED by $4,000 (0.7%) on 04/23/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1935 Built: 1994Monthly Fee: $58 Tax: $4,248 (2025)Community: Paddocks WestSpa: NoSingle Family
Taxes:$4,248
Elementary School: Tatum Ridge Elementary
Tax Year: 2025
Middle School: McIntosh Middle
Remarks: Under contract-accepting backup offers. 2304 Seattle Slew Dr, Sarasota — Immaculate, move-in ready single-family home in a quiet neighborhood with a convenient location. This inviting residence features an open living area anchored by a cozy fireplace, plenty of light, vaulted ceilings, no carpet anywhere and easy-care luxury vinyl plank flooring throughout, a modern kitchen, and a private pool with generous outdoor entertaining space framed by new pavers and landscaping. Updates & upgrades include: 2022 — pool resurfaced, pool heater installed, interior and exterior paint refreshed; 2023 — new AC, luxury vinyl plank (no carpet) installed throughout, new privacy fence; 2024 — quartz countertops and updated cabinetry in the kitchen; 2025 — all-new windows and exterior doors, new appliances, new pavers, new gutters, refreshed landscaping, new pool motor and LED pool light. Conveniently located near The Celery Fields, beaches, top-rated schools, University Town Center, and Waterside. This turnkey home blends contemporary finishes with reliable systems for comfortable Sarasota living. Schedule a showing to see the full scope of improvements.
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: Jason Caller (941-301-5083)
4242 MADEIRA CT #3315, SARASOTA, FL 34233
$279,000110 Days on yellowkey MLS ID: A4685842
REDUCED by $10,000 (3.5%) on 06/07/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1063 Built: 1989Monthly Fee: $458 Tax: $1,180 (2025)Community: Casa Del Sol Sec ViiCondo
Taxes:$1,180
Elementary School: Ashton Elementary
Middle School: Sarasota Middle
Remarks: Move-in ready and thoughtfully updated, this beautiful 2-bedroom, 2-bathroom end-unit home offers the perfect combination of comfort, style, and scenic surroundings. The inviting interior features an open and airy layout, enhanced by hurricane-impact windows and a hurricane-rated sliding glass door for both safety and peace of mind. Elegant plantation shutters add a refined touch, while a built-in TV with an electric fireplace creates a warm and cozy living area. The eat-in kitchen is ideal for casual dining offering ample space and functionality. The primary suite serves as a private retreat, complete with a walk in closet and a beautifully updated ensuite bath featuring high-end finishes, including a custom-made vanity sourced from North Carolina. The primary bathroom has been tastefully renovated within the last two years. Additional major upgrades include a full plumbing repipe, along with a water heater, washer, and dryer all replaced just two years ago—ensuring modern efficiency and reliability. One of the standout features of this home is the converted, air-conditioned back patio, perfect for use as a sunroom, home office, or additional living space to enjoy year-round comfort while taking in the tranquil lake views. Located in the desirable Casa Del Sol community, residents enjoy a vibrant lifestyle with amenities including tennis and pickleball courts, shuffleboard, bocce ball, a heated pool for cooler months, and a clubhouse with a pool, poker tables, a gym, books and endless ongoing activities. Conveniently situated near I-75, this home is just a short drive to Siesta Beach, University Town Center, Waterside, and downtown Sarasota—offering easy access to shopping, dining, and the world-renowned Gulf Coast beaches. This exceptional home truly offers the best of Florida living—schedule your showing today!
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Carey Hibbs (941-915-9235)
5155 HIDDEN HARBOR RD, SARASOTA, FL 34242
$1,995,000184 Days on yellowkey MLS ID: G5107159
2 Days Off yellowkey (back on 6/10/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2233 Built: 1973Monthly Fee: $332 Tax: $7,806 (2025)Community: Hidden HarborSpa: NoSingle Family
Taxes:$7,806
Elementary School: Phillippi Shores Elementary
Remarks: Nearly 200 feet of deep-water frontage in the prestigious Hidden Harbor enclave of Siesta Key—no bridges, quick access to Roberts Bay and the Gulf of America. Move-in ready and never flooded. Enjoy island living in this private waterfront setting surrounded by multi-million dollar estates. Lush, canopy-lined brick paver streets, wide water views, no through streets, and excellent boating access. The home has been thoughtfully renovated with an emphasis on functionality and storage, featuring an updated kitchen, modernized bathrooms, tile flooring throughout, recessed lighting, impact-rated windows and sliders, landscape lighting, a dedicated well with irrigation system, and a heated saltwater pool. Bike to the award-winning Siesta Key Beach, dine and shop in Siesta Village, kayak from your dock to nearby mangrove tunnels, or enjoy the convenience of downtown Sarasota less than seven miles away. A rare waterfront home offering immediate enjoyment and long-term upside in a neighborhood experiencing significant luxury redevelopment.
Listing is courtesy of: LIST NOW REALTY, LLC (352-385-7636)
Listing Agent: Matt Buttner (352-385-7636)
2816 MICHIGAN ST, SARASOTA, FL 34237
$379,000103 Days on yellowkey MLS ID: A4689787
REDUCED by $20,500 (5.1%) on 06/05/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1380 Built: 1956 Tax: $872 (2025)Community: Glen RidgeSingle Family
Taxes:$872
Elementary School: Alta Vista Elementary
Middle School: Booker Middle
Remarks: SAY HELLO TO A GOOD BUY * SOLAR PANELS ARE OWNED (not leased), HOUSE IS KEPT AT 74 DEGREES AND THE HIGHEST POWER BILL IS $50+/-/MONTH WHICH IS AN ESTIMATED SAVINGS OF ABOUT $200/MONTH * This home has been LOVINGLY RENOVATED * NEW Kitchen with NEW Cabinets & Countertops & NEW Appliances * NEW Bathroom with NEW Vanity & NEW Shower * NEW Tile Flooring * NO Carpet * NEW Paint * Metal Roof * Solar Panels so you have a very low electric bill * LARGE Carport & Storage Room * This house is beautiful with a very large Living Room & Dining Room - there's a lot of A/C Living Space * Spacious Front Yard * Paver Park area is located in a great school district * You are minutes to Payne Park and a few blocks to The Legacy Trail * Short bike ride to Downtown and the Bay Front * Short car ride to Selby Botanical Gardens, Siesta Key, St Armand's Circle & Lido Beach * This is an EXCELLENT year round home OR winter getaway * One look & you'll fall in love * Run, don't walk to this INCREDIBLE VALUE *
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Glenn Brown (941-342-6464)
707 S GULFSTREAM AVE #505, SARASOTA, FL 34236
$695,000222 Days on yellowkey MLS ID: A4675101
0 Days Off yellowkey (back on 5/30/2026)
REDUCED by $104,000 (13.0%) on 05/15/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1240 Built: 1974 Tax: $6,333 (2024)Community: Essex HouseSpa: NoCondo
Taxes:$6,333
Remarks: Be prepared for the breathtaking, UNOBSTRUCTED BAY VIEWS from this exquisite condominium in the Essex House – one of downtowns most coveted addresses and among the few residences untouched by neighboring development. Exquisitely positioned showcases breathtaking vistas of Siesta Key, Sarasota Big Pass, Marina Jack and Downtown Sarasota. From dramatic floor-to-ceiling windows, enjoy a front-row seat to Sarasota's legendary sunsets every evening. This thoughtfully updated 2+ bedroom, 2 bath residence blends sophistication with comfort. Coffered ceilings with recessed lighting and a built-in electric fireplace create an inviting ambiance - perfect for relaxing as the sun dips into the Gulf. The contemporary kitchen is as functional as it is stylish, featuring stainless steel appliances, open shelving, and expansive quartz countertops ideal for entertaining. The redesigned primary suite offers a serene private retreat, complete with a custom closet, built-in desk area, bench seating with additional storage, dual vanities with quartz countertop, and a beautifully appointed walk-in shower. You will appreciate the clean lines of wood imprinted porcelain tile flooring throughout, additional storage, built-in bookcases and washer/dryer. A true showpiece of the home is the fully enclosed glass Florida Room - an airy and seamless extension of the living space accessible from the living area and both bedrooms. Surrounded by glass and equipped with screens, it is the perfect setting for morning coffee or evening cocktails while soaking in the ever-changing, memorizing views. Located in the vibrant heart of downtown, you are just steps from award-winning dining, theatres, galleries, boutique shopping, and Whole Foods. Residents of the Essex House enjoy premier amenities include a fitness center, pool deck, security, covered garage parking with an assigned space, and pet-friendly living. This is a rare opportunity to own unobstructed water views paired with refined downtown luxury - plus the added peace of mind that all assessments have been paid.
Listing Agent: Scott Rickards, Pa (941-356-7040)
332 BOB WHITE WAY, SARASOTA, FL 34236
$4,300,00067 Days on yellowkey MLS ID: A4690146
Bed: 3 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 2987 Built: 2027Monthly Fee: $110 Tax: $14,705 (2025)Community: Bird Key SubSpa: YesSingle Family
Taxes:$14,705
Remarks: Pre-Construction. To be built. With a fresh, exciting floor plan and stylish coastal flair, this exquisite new Bird Key residence is set on a 1/3-acre homesite in one of Sarasota’s most coveted boating communities. Located just over the Ringling Bridge from the mainland, Bird Key is centrally located between the Downtown arts and cultural district and world-renowned St. Armand’s Circle. Designed by the award-winning professionals at Allegra Homes, the “Lauren Coastal” showcases 2,987 sq. ft. of open living with 3 ensuite bedrooms, a dedicated office with custom built-ins, and a poolside bonus room with wet bar. The foyer entry invites exploration into a fabulous great room, an amazing dream kitchen, and a dining area with built-in buffet. The bright, open great room features a striking volume ceiling with architectural accents, floor-to-ceiling entertainment wall with fireplace, and wide glass sliders opening to a fantastic outdoor setting. Enclosed in Clear View screening, the covered lanai is enhanced with wood tongue-and-groove ceiling, a heated saltwater pool/spa, and a grilling station with beverage center. The kitchen is a standout centerpiece, anchored by a large island and appointed with premium name brands such as Sub-Zero and Wolf, including a 42-inch refrigerator, wine cooler, 36-inch cooktop, oven, drop-down microwave, and dishwasher. The secluded owner’s suite offers casual comfortability with its dramatic headboard feature wall, roomy sitting area and stunning bath highlighted by a freestanding soaking tub, an 80” tall frameless glass shower enclosure, floating full-height mirrors, split vanities, and a private water closet. Additional features include trey ceilings with cove molding, recessed lighting, finished closets, 8-ft. solid-core interior doors, hurricane shutters, a tankless recirculating water heater, and an upgraded trim package in the great room, dining room, and foyer. A brick paver driveway leads to the 3-car garage, and the beautiful exterior façade is framed in a lush landscape with irrigation system and night lighting for added visual appeal. Residents can enjoy the Bird Key Yacht Club’s exclusive social club experience for its members with a wide array of outstanding amenities and social events focused around boating, dining and tennis in a prized bayfront setting. With completion in late 2026, the $27.5 million rebuild will include a 21,500-sq-ft clubhouse plus 3,500 sq-ft of covered outdoor decks, a new pool, relocated bocce courts, and a fourth tennis court. Bird Key is the standard for exceptional Florida living and this beautiful address is no exception. It’s the perfect opportunity to live an enviable island lifestyle in a prestigious enclave surrounded by the pristine waterways of Sarasota Bay.
Listing is courtesy of: GRECO REAL ESTATE (941-685-0449)
Listing Agent: Karen Greco (941-504-6927)
509 SPOONBILL WAY, SARASOTA, FL 34236
$4,350,00067 Days on yellowkey MLS ID: A4691908
Bed: 3 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 2987 Built: 2027Monthly Fee: $110 Tax: $6,764 (2025)Community: Bird Key SubSpa: YesSingle Family
Taxes:$6,764
Remarks: Under Construction. With a fresh, exciting floor plan and sophisticated modern flair, this exceptional new residence in Bird Key is perfectly positioned on an oversized quarter-acre-plus homesite within one of Sarasota’s most prestigious boating communities. Ideally located just across the John Ringling Causeway, Bird Key offers effortless access to both vibrant downtown Sarasota and the world-renowned St. Armands Circle. Crafted by the award-winning team at Allegra Homes, the stunning “Lauren Modern” design features 2,987 square feet of thoughtfully curated living space with 3 ensuite bedrooms, a private office with custom built-ins, and a versatile poolside bonus room complete with wet bar. A welcoming foyer opens into an impressive great room where soaring architectural ceilings, a dramatic floor-to-ceiling entertainment wall with fireplace, and expansive walls of glass create an atmosphere that is both refined and inviting. Wide sliding doors seamlessly connect the interior living spaces to an extraordinary outdoor retreat designed for year-round enjoyment. Enclosed with Clear View screening, the covered lanai showcases a wood tongue-and-groove ceiling, heated saltwater pool and spa, and a fully appointed outdoor grilling station with beverage center—ideal for entertaining or relaxed coastal living. At the heart of the home, the designer kitchen blends beauty and functionality with an oversized island and premium appliances from Sub-Zero and Wolf, including a 42-inch refrigerator, wine cooler, 36-inch cooktop, wall oven, microwave drawer, and dishwasher. Privately tucked away, the owner’s suite is a luxurious sanctuary featuring a dramatic feature wall, spacious sitting area, and lavish bath with freestanding soaking tub, oversized frameless glass shower, floating mirrors, split vanities, and private water closet. Additional appointments include tray ceilings with cove molding, recessed lighting, finished closets, 8-foot solid-core doors, hurricane protection, tankless recirculating water heater, and upgraded trim detailing throughout the main living areas. A circular brick paver driveway leads to the spacious 3-car garage, while professionally designed landscaping, irrigation, and evening accent lighting enhance the home’s striking curb appeal. Residents of Bird Key also enjoy the opportunity to join the exclusive Bird Key Yacht Club, offering a distinguished social lifestyle centered around boating, dining, tennis, and waterfront recreation. The club’s exciting $27.5 million transformation—scheduled for completion in late 2026—will introduce an impressive new clubhouse, expanded outdoor gathering spaces, resort-style pool, additional tennis court, and enhanced amenities. Combining luxury, location, and timeless coastal sophistication, this remarkable property presents a rare opportunity to experience the very best of Sarasota waterfront living in one of the region’s most popular island enclaves.
8501 MIDNIGHT PASS RD, SARASOTA, FL 34242
$29,995,00076 Days on yellowkey MLS ID: A4692839
Bed: 6 Bath: 8.5 Gar: 7 Liv Area Sq Ft: 12000 Built: 2024 Tax: $141,465 (2025)Community: Siesta KeySpa: YesSingle Family
Taxes:$141,465
Remarks: Set across nearly three acres of pristine waterfront on Siesta Key, Crystal Waters is the most significant private estate in Sarasota—a once-in-a-generation offering that redefines luxury living on Florida’s Gulf Coast. With extraordinary scale, architectural pedigree, and 217 feet of direct Sarasota Bay frontage, this landmark property represents a level of craftsmanship, beauty, and exclusivity rarely seen in the region. Designed by renowned architectural firm Stofft Cooney Architects and custom-built by Chris Jorgensen of Florida West Builders, the Palm Beach-inspired estate encompasses 10,267 square feet with five bedrooms, six full baths, and two half baths. Surrounded by lush tropical gardens and panoramic bay views, every aspect of the property has been conceived to deliver an unparalleled waterfront lifestyle. A dual-gated arrival along a Tabby seashell drive leads to a stately façade framed by towering palms and a grand porte cochère. Beyond solid mahogany doors, a magnificent foyer welcomes guests with travertine floors inlaid with cabochon stone and a sweeping staircase featuring hand-crafted Chippendale railings. Walls of impact glass dissolve the boundary between indoors and out, filling the residence with natural light and uninterrupted views of Sarasota Bay. Refined details include a natural gas fireplace with imported limestone hearth, hand-crafted Vitali European oak flooring in a warm Milano finish, custom millwork, and a serene palette of coastal hues. The kitchen is both a showpiece and gathering place, appointed with custom Campbell cabinetry, Cristallo quartzite surfaces, a custom La Cornue range, dual islands, and walk-in and butler’s pantries. A bayfront breakfast nook and formal dining room open seamlessly to expansive waterfront terraces. Nearby, the clubroom showcases hand-painted Gracie chinoiserie panels, vaulted cypress ceilings, and a wet bar. The first-floor primary suite serves as a private sanctuary overlooking the bay, with French doors opening to the pool terrace. Custom dressing rooms and spa-inspired baths surround a striking octagonal vestibule featuring New Ravenna mosaic floors, Calacatta Matarazzo quartzite, a soaking tub, and marble-clad shower. Upstairs, guest suites, a lounge, and an exercise room provide exceptional accommodations. An Old Florida-style guest residence above a four-car garage offers Pecky Cypress-lined interiors, vaulted ceilings, a full kitchen, covered balcony, and spacious bedroom suite. The main residence is further complemented by an oversized three-car garage. Outdoors, winding pathways lead through beautifully curated grounds to a spectacular 56-foot vanishing-edge saltwater pool that appears to merge with the bay beyond. A covered waterfront pavilion with fireplace, summer kitchen, and tongue-and-groove ceiling creates an elegant setting for entertaining. A private tennis court and lighted pavilion with lounge and fireplace complete the resort-caliber amenities. Along the shoreline, a 90-foot dock extends into Little Sarasota Bay and features a floating kayak launch and a 20,000-pound lift capable of accommodating a 34-foot vessel. Crystal Waters is more than a residence—it is Sarasota’s defining waterfront estate. Unmatched in scale, setting, craftsmanship, and provenance, it stands as one of the finest private properties ever created on Florida’s Gulf Coast. Available lot for sale directly across the street enjoys beach access.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kim Ogilvie (941-951-6660)
6308 MIDNIGHT PASS RD #6, SARASOTA, FL 34242
$995,000389 Days on yellowkey MLS ID: A4657483
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1232 Built: 1965Monthly Fee: $1,005 Tax: $5,582 (2025)Community: Crescent ArmsSpa: NoVilla
Taxes:$5,582
Remarks: Coastal Luxury Villa with Thai-Inspired Elegance Now Offered at $995,000 Experience the best of Siesta Key living in this beautifully renovated two-bedroom, two-bath villa located in the highly sought-after, gated beachfront community of Crescent Arms. Now priced at $995,000, this is a compelling opportunity recently adjusted from $1,075,000 to reflect today’s market and create immediate value. This thoughtfully updated residence blends custom coastal finishes with subtle Thai-inspired design, creating a warm, serene atmosphere throughout. The open-concept layout offers seamless flow between the kitchen, dining, and living areas ideal for both everyday living and entertaining. The gourmet kitchen features quartz countertops, stainless steel appliances, and generous workspace, all opening into a bright and inviting living area. Both bathrooms have been tastefully updated with spa-like finishes, including a walk-in shower and modern fixtures. Step outside to your private patio perfect for relaxing, grilling, or enjoying the tropical surroundings just moments from the beach. Crescent Arms offers exclusive private beach access to world-famous Siesta Key Beach, along with onsite management making this an excellent option for personal use, vacation rental income, or a combination of both. This property has a proven rental history with strong year-round bookings. Whether you’re searching for a coastal retreat, investment opportunity, or both, this villa delivers location, lifestyle, and value. Sold turnkey move right in or start generating income immediately.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Derek Edwards (941-929-3183)
2231 WOOD ST, SARASOTA, FL 34237
$1,999,000302 Days on yellowkey MLS ID: A4666469
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2731 Built: 2024 Tax: $4,662 (2023)Community: Poms Park 3Spa: YesSingle Family
Taxes:$4,662
Tax Year: 2023
Remarks: This exquisite new-construction modern residence by Milano Homes, situated on an expansive double lot in the heart of Sarasota, blends elegance, convenience, and investment opportunity. Located within Sarasota city limits, this property qualifies for weekly rentals in one of the area’s most in-demand markets—a highly desirable option that allows for a strong six figure range income annually. This single-story home offers the ultimate in comfort with no stairs to navigate, featuring four spacious bedrooms, three-and-a-half designer bathrooms, and a two-car garage. The outdoor living space is a private sanctuary, complete with a sparkling pool and spa, outdoor shower, and a large fenced yard ideal for both relaxation and entertaining. As with all Milano Homes, the interiors showcase exceptional craftsmanship and imported Italian finishes. From the state-of-the-art kitchen—equipped with Subzero refrigeration, a Wolf induction cooktop, and Wolf oven—to the custom Italian cabinetry, fixtures, and flooring, every detail exudes sophistication. The open-concept living area flows seamlessly into the outdoor retreat, creating the perfect setting for gatherings and indoor-outdoor living. Perfectly positioned, this property offers easy access to the newly extended Legacy Trail, making it a haven for bikers, runners, and nature lovers. Downtown Sarasota’s vibrant arts, dining, and marina scene is just minutes away, while Siesta Key’s award-winning beaches and St. Armands Circle’s luxury shopping and dining are only a five-minute drive. Whether you’re seeking a full-time residence, seasonal retreat, or an income-producing short-term rental, this home offers an unmatched opportunity to enjoy and invest in the Sarasota lifestyle. Work hand-in-hand with the dedicated Milano Homes professionals to personalize this custom residence, creating a one-of-a-kind dream home tailored just for you.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Rinat Sikdar (941-993-9292)
3219 CAMBRIDGE DR, SARASOTA, FL 34232
$349,00083 Days on yellowkey MLS ID: A4692358
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1116 Built: 1961 Tax: $3,420 (2025)Community: Sarasota SpgsSingle Family
Taxes:$3,420
Elementary School: Brentwood Elementary
Remarks: Lovely, well maintained 3 Bed/2 Bath home located on quiet street in established neighborhood convenient to everything! Large yard with room for pool or create your own backyard oasis. 3rd bedroom could be office/studio. New roof 2024 , updated electrical panel, newer windows. This home is in perfect condition. Move in ready!
Listing is courtesy of: GOOD CHOICE REALTY INC. (941-355-8282)
Listing Agent: James Good (941-355-8282)
2165 SUNNYSIDE LN, SARASOTA, FL 34239
$569,00061 Days on yellowkey MLS ID: A4690142
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1022 Built: 1952 Tax: $5,683 (2025)Community: Hibiscus Park 1Spa: NoSingle Family
Taxes:$5,683
Remarks: Great Opportunity to own your own Mid Century block built cottage near Sunnyside Park, Arlington Park and Sarasota Memorial Hospital, Or build NEW on the 9681 sq ft lot.... Ready to move right in, this 2 bedroom 1 bath home ...Enjoy the great back yard. AC 2014, Roof 2019.. Hot Water Heater 2020.....Located within the City of Sarasota limits, this home allows for weekly (7-day minimum) rentals, making it uniquely suited for those seeking both personal enjoyment and income potential.
Listing is courtesy of: MEDWAY REALTY (941-375-2456)
Listing Agent: Jonathan Woods (941-356-7583)
2940 BOUGAINVILLEA ST, SARASOTA, FL 34239
$650,000102 Days on yellowkey MLS ID: A4689977
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1710 Built: 1960Monthly Fee: $17 Tax: $6,279 (2025)Community: South GateSingle Family
Taxes:$6,279
Remarks: Stunning, mid-century modern home in highly desirable South Gate with views you must see to believe! If you could have picked one of the best lots in South Gate back in the 1960’s this may have been it. The two-bedroom plus office, two bath home sits on a bluff overlooking a wide portion of Philippi Creek including a large aquatic preserve. You’ll be mesmerized by long, unobstructed views in every direction. A nature lovers delight and absolutely intoxicating. But while location is important, there are many more features in this classic home to consider. Entering through the large foyer you’ll immediately notice beautiful terrazzo floors throughout and a great room with vaulted ceilings. There’s an adjacent dining area off the kitchen and all of these spaces look out through what appears to be a “wall of glass” dedicated to the world class view of flora and fauna. The primary bedroom also has views and access to the back yard and the primary bathroom has been upgraded with a separate tub and walk in shower. The den/office can be made more private with sliding pocket doors and function as a guest bedroom. It even has a dedicated, enclosed patio and garden space. There’s an attached, oversized garage with room for your workshop and a double wide driveway with plenty of parking. While this home has been appropriately updated and improved over the years you’ll find it’s all been done with a great sensibility to the original intent, quality and “hipness” so many are learning to appreciate, again.
Listing Agent: Barbara May (404-822-9264)
771 JOHN RINGLING BLVD #7, SARASOTA, FL 34236
$529,500331 Days on yellowkey MLS ID: A4663602
REDUCED by $20,000 (3.6%) on 04/23/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 938 Built: 1965 Tax: $5,888 (2024)Community: Sarasota Harbor EastCondo
Taxes:$5,888
Middle School: Pine View School
Remarks: Direct Waterfront, newly updated 2 bedroom 2 bath end unit with hurricane resistant windows and sliders. Sarasota Harbor East, a premier 55+ maintenance-free community in one of the most desirable bayfront locations in Sarasota! Just minutes from downtown Sarasota, St. Armands Circle, Lido Beach, and directly across from the Sarasota Yacht Club, this community offers an unmatched combination of convenience, charm, and waterfront living. This residence features a fully glass-enclosed lanai—perfect for soaking in the spectacular waterfront views. The unit also comes with a covered parking space plus ample guest parking. Community highlights include: Free boat docks for sailboats or powerboats up to 30’ (first-come, first-serve), heated waterfront pool with stunning bay views, community gas grill and picnic area, secured covered bicycle shed & kayak storage, individual storage bins for residents. With its unbeatable location, Sarasota Harbor East is a rare opportunity to own in one of Sarasota’s most sought-after waterfront communities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Janice Melzer Langa (941-404-0802)
1829 BOUGAINVILLEA ST, SARASOTA, FL 34239
$4,100,00051 Days on yellowkey MLS ID: A4695800
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4857 Built: 1925 Tax: $13,902 (2024)Community: Poinsettia Park 2Spa: YesSingle Family
Taxes:$13,902
Remarks: Experience the timeless charm and distinctive elegance of this West of Trail luxury cottage, with modern finishes that remain true to its original allure, at 1829 Bougainvillea Street. Occupying three lots, it is nestled gracefully in Sarasota's most cherished neighborhood. Set on a tranquil, tree-lined avenue, moments from vibrant Southside Village, Sarasota Memorial Hospital, and the renowned sands of Siesta Key, this thoughtfully enhanced residence exudes a rare character and allure that newer homes simply cannot replicate. From the moment you step inside, you're captivated by a refined blend of historic charm and contemporary luxury. Rich hardwood flooring, detailed crown moldings, and designer lighting create a warm and refined ambiance throughout the spacious, open-concept layout. Anchoring this home is a beautifully reimagined gourmet chef's kitchen, showcasing high-end stainless steel appliances, luminous granite countertops, bespoke cabinetry, and an expansive island—ideally suited for gatherings both grand and intimate. The luxurious master suite is a serene retreat, illuminated by abundant natural light and offering generous closet space alongside a spa-inspired ensuite with a sumptuous walk-in shower and dual vanities. Additional bedrooms and versatile living areas effortlessly accommodate family, guests, or a tailored home office. Unique to this remarkable residence is the thoughtfully designed separate living quarters, complete with a private entrance, an inviting bedroom, a fully equipped kitchen, and a full bathroom. Ideal for hosting guests, housing extended family, or offering privacy to long-term visitors, these quarters are unique. Outside, the magic only continues—enchanting gardens burst with colorful bougainvillea, and mature greenery surrounds an inviting patio that effortlessly extends the living space outdoors, perfect for sunlit gatherings or quiet moments beneath Sarasota's famous skies. With meticulous care and modern upgrades, including a newer roof, advanced HVAC systems with two newly installed air conditioning units, recently replaced front-facing windows, and fully updated plumbing and electrical infrastructure, this home blends historic character with contemporary convenience, ensuring comfort, efficiency, and peace of mind. 1829 Bougainvillea Street represents more than just a renowned address; it offers a rare opportunity to own a property rich in Sarasota history and charm, distinctively set apart from uniformity and infused with authentic character. Welcome home to an extraordinary residence awaiting your personal story. Its roots run deep into our community. The prior owners have all remained friends to this day, and the resurgence of the modern cottage is now at the forefront of interior design and architecture. This property embodies that trend in a way no other home can. A true one-of-a-kind that will never be replicated.
Listing Agent: Ryan Skrzypkowski (941-328-8307)
435 S GULFSTREAM AVE #1103, SARASOTA, FL 34236
$635,000111 Days on yellowkey MLS ID: A4688618
0 Days Off yellowkey (back on 6/5/2026)
REDUCED by $30,000 (4.5%) on 05/22/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1424 Built: 1972 Tax: $8,550 (2025)Community: Regency HouseSpa: NoCondo
Taxes:$8,550
Remarks: One or more photo(s) has been virtually staged. Elevated PENTHOUSE living with breathtaking views. Ready to skip the renovations and some carrying costs? This 11th-floor penthouse-level gem at Regency House is officially “THE ONE”. Spanning 1,424 SF of bright, open space, this 2-bed, 2-bath residence trades dark corners for floor-to-ceiling glass that frames Sarasota Bay and the Ringling Bridge like a living gallery. Inside, a clean, neutral palette creates a move-in-ready aesthetic that complements a variety of design styles. The designer kitchen featuring custom cabinetry and stone surfaces flows effortlessly into an open-concept living area anchored by a custom electric fireplace, perfect for sunset hosting. Retreat to a spacious primary suite with tranquil water views, complemented by a well-sized secondary bedroom ideal for guests or a home office. Both bathrooms have been tastefully updated. A new in-unit washer and dryer add everyday convenience, along with additional in-unit storage closets. Enjoy maintenance-free living with a professional on-site manager and 24-hour concierge, dedicated covered parking, heated community pool and fitness center, club room, and an active social calendar. Ideally positioned on the quiet edge of downtown Sarasota, this residence offers a true world-class lifestyle just moments from Marina Jack, boutiques of Palm Avenue, Opera and Theatre, Whole Foods, and the botanical beauty of Selby Gardens. Whether it's a morning walk through Bayfront Park or a quick drive over the bridge to St. Armand's Circle and Lido Beach, the best of the Gulf Coast is quite literally at your doorstep. Celebrate ease of ownership and peace of mind; in an era where buyers are cautious about condo buildings, Regency House stands apart as a solid choice. This building has completed the Milestone Inspection and Structural Integrity Reserve Study and maintains healthy reserves. To make your transition entirely frictionless, the seller will pay the Special Assessment for the upgraded pool.
Listing Agent: Dana Cook Westmark (941-356-5091)
1035 SEASIDE DR #603, SARASOTA, FL 34242
$4,600,000250 Days on yellowkey MLS ID: A4672418
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2303 Built: 2023 Tax: $43,735 (2024)Community: Ten35 SeasideSpa: YesCondo
Taxes:$43,735
Remarks: Discover the epitome of luxury living at this stunning beachfront residence, offering an unparalleled blend of modern elegance and coastal serenity. Situated on the penthouse level overlooking the pristine quartz sand of Siesta Key’s Crescent Beach, this exclusive location promises breathtaking Gulf views, stunning sunsets, direct beach access, world class amenities and is perfect for those seeking the ultimate in sophistication and relaxation. Every inch of the 2,562 total square feet of this three bedroom, three and one half bathroom condo has been thoughtfully designed to curate comfort and convenience. The living space, adorned with fetching furnishings and charming décor, offers an open concept with seamless indoor to outdoor integration to the spacious patio and outdoor kitchen with panoramic views of the horizon and when privacy or shade is in order, utilize the advantageous motorized blinds for added comfort. The chef’s kitchen, featuring top of the line cabinetry draped in quartz countertops and state of the art appliances featuring a Wolf gas range, is a masterpiece where inspired coastal cuisine will be a pleasure to create. Preserve your prized wine collection in the attractive wine refrigerator. A true retreat, the luxurious primary suite offers mesmerizing views, a spacious walk-in closet and a spa-inspired ensuite bathroom complete with dual sinks and a glass enclosed shower with multiple shower heads. The two additional bedrooms are generously sized, each offering ample closet space and easy access to elegant ensuite guest bathrooms. From the handsome natural wood flooring to the eye-catching and dazzling light fixtures, this Siesta Key dwelling is intentional in its purpose of granting a tranquil island paradise to you, your loved ones and your furry family members as pets are welcome. For the owner with an interest in income potential, a full service on site rental manage
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Rudy Dudon (941-234-3991)
1011 BACON AVE, SARASOTA, FL 34232
$299,900170 Days on yellowkey MLS ID: A4681625
0 Days Off yellowkey (back on 3/6/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1161 Built: 1983 Tax: $3,427 (2025)Community: Highland Crest 2Single Family
Taxes:$3,427
Elementary School: Fruitville Elementary
Remarks: Short Sale. Move-In Ready Home Near Pinecraft with Garage and Room to Grow Tucked away on a quiet dead-end street, this well-maintained 2 bedroom, 2 bathroom home offers privacy, flexibility and a central Sarasota location with no HOA fees or restrictions. From the moment you enter, the home feels open and inviting, with long sightlines and connected living spaces that create a natural sense of flow. The living and dining areas are open to one another, giving the home an airy feel while still maintaining defined spaces. Crown molding adds subtle character and ceramic tile flooring throughout provides durability and easy upkeep. The layout allows natural light to travel through the home, enhancing the sense of space and openness. The kitchen sits at the heart of the home and connects seamlessly to both the living and dining areas. Generous counter space, ample cabinetry and a long serving bar make it functional for everyday living while also working well for gatherings. Sliding glass doors bring in additional light and lead to the screened-in lanai, extending the living space outdoors. The primary suite offers a comfortable retreat with a large walk-in shower, while the second bedroom provides flexibility for guests, a home office, or additional living needs. Outside, the fully fenced backyard offers privacy and room to relax or entertain. A one-car garage and extra-wide driveway provide convenient parking and storage. Key improvements have already been completed, including a new septic tank and drain field (2019), A/C replacement (2021), and water heater (2022), along with a whole-home water filtration system. Centrally located in Sarasota, this home is just minutes from shopping, dining, beaches, public transportation, and the unique charm of Pinecraft!
Listing is courtesy of: KW SUNCOAST (941-792-2000)
Listing Agent: Ronald Pepka (941-877-1488)
5572 SHADOW LAWN DR, SARASOTA, FL 34242
$4,795,00052 Days on yellowkey MLS ID: A4695248
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3523 Built: 2027Monthly Fee: $17 Tax: $5,171 (2026)Community: Siesta IslesSpa: YesSingle Family
Taxes:$5,171
Tax Year: 2026
Remarks: Under Construction. An exceptional opportunity to own a brand-new waterfront residence in the highly sought-after Siesta Isles community. Expertly crafted by Nutter Custom Construction, this British West Indies-inspired custom home offers 3,568 square feet of air-conditioned living space and 5,725 total square feet designed for luxurious coastal living. Situated on a 14,300-square-foot lot with 104 feet of waterfront and a brand-new seawall, this thoughtfully designed residence features 4 bedrooms, 4.5 bathrooms, a 2-car garage, private pool and spa, and an expansive outdoor living area complete with a summer kitchen. Interior features include soaring 23.5-foot ceilings in the entry & foyer, 11.4-foot ceilings throughout the main living areas, custom wood beam details, wide-plank wood flooring, custom cabinetry, natural stone finishes, and a premium Thermador appliance package. The well-designed floor plan offers a first-floor primary suite, spacious great room, and seamless indoor-outdoor living. Upstairs, a flexible bonus room showcases dramatic glass corner sliders opening to a waterfront balcony with sunset views. The luxurious primary suite features a private lanai, spa-inspired bath with outdoor shower, and oversized walk-in closets. Located just minutes from Siesta Key Village and world-renowned Siesta Key Beach, this exceptional property combines the best of waterfront living with convenient access to dining, shopping, and entertainment. Buyers may have the opportunity to make select finishes and customization choices depending on the stage of construction. Estimated completion February 2027. Experience the unmatched craftsmanship and attention to detail that define every Nutter Custom Construction home.
Listing is courtesy of: NCC PROPERTIES LLC (941-924-1868)
Listing Agent: Morgan Marziali (941-806-7214)
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