Location: Sarasota
Keyword(s): Sarasota High
Keyword(s) High School: Sarasota High
Do Not Show Listings
3422 FENWAY DR, SARASOTA, FL 34232
$325,00036 Days on yellowkey MLS ID: N6144623
1 Days Off yellowkey (back on 6/11/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1264 Built: 1973 Tax: $2,567 (2025)Community: Sarasota SpgsSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,567
Elementary School: Brentwood Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: McIntosh Middle
Remarks: Under contract-accepting backup offers. Welcome to this beautifully updated and meticulously maintained 3-bedroom, 2-bathroom home offering just under 1,300 square feet of comfortable and functional living space in the heart of Sarasota. Whether you’re searching for a primary residence, vacation getaway, or income-producing investment property, this home checks all the boxes. Designed with a desirable split floor plan, this home offers privacy and convenience for both homeowners and guests. The oversized primary suite serves as a peaceful retreat, featuring a spacious bedroom, large walk-in closet, and a private en-suite bathroom. Two additional bedrooms and a full guest bathroom are thoughtfully positioned on the opposite side of the home. Step inside and appreciate the many recent updates throughout, including newer kitchen cabinets, updated countertops, beautiful flooring, and fresh interior and exterior paint, creating a stylish and move-in-ready living space. The home features no carpet throughout, offering easy maintenance and a clean, modern feel. Being sold fully turnkey furnished, this property allows you to move right in or begin generating rental income immediately. The inviting living spaces flow seamlessly to the oversized screened-in lanai, providing the perfect place to relax, entertain guests, or enjoy Florida’s year-round sunshine. Outside, you’ll find a large, fully fenced backyard with plenty of room for pets, play, gardening, or even the future addition of a pool. For added peace of mind, the home is equipped with brand-new built in accordion hurricane shutters on every window, providing both convenience and storm protection. Located in one of Sarasota’s most desirable areas, this property offers no rental restrictions, making it an exceptional opportunity for investors, seasonal residents, first-time homebuyers, or those searching for their forever home. Enjoy being just minutes from world-famous Siesta Key Beach, exceptional dining, shopping, entertainment, parks, and top-rated schools. This move-in-ready home combines modern updates, flexibility, and an unbeatable location—all in one exceptional package. Whether you’re looking for a full-time residence, a seasonal retreat, or a strong investment opportunity, this Sarasota gem is ready to impress. IMPORTANT ITEMS: AC REPLACED IN 2022, HOT WATER HEATER REPLACED IN 2021, ROOF REPLACEMENT 2017. Schedule your tour today!
Listing is courtesy of: CORNERSTONE R.E OF SW FL (941-404-4620)
Listing Agent: Ashley Leroy (941-724-1621)
1691 FLEETWOOD DR, SARASOTA, FL 34232
$438,500182 Days on yellowkey MLS ID: A4678015
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1701 Built: 1977Monthly Fee: $18 Tax: $4,515 (2025)Community: TamaronSingle Family
Taxes:$4,515
Elementary School: Alta Vista Elementary
Remarks: Welcome to Tamaron! This home is situated on an oversized lot with serene lake views. This 3-bedroom, 2.5-bath home offers space, comfort, and an ideal central Sarasota location. A brand-new roof adds peace of mind, making this home a smart and inviting opportunity. Inside, the open floor plan seamlessly connects the dining room, living room, and family room, creating an expansive layout perfect for both everyday living and entertaining. The home’s generous proportions provide flexibility and a true sense of openness throughout. Enjoy tranquil lake views from your backyard while still being just minutes from it all. Centrally located near Pinecraft, this home is a short drive to top restaurants, shopping, downtown Sarasota, and the world-renowned Siesta Key Beach. With its spacious design, oversized lot, and prime location, this Tamaron home offers the perfect blend of privacy, convenience, and Florida lifestyle living.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Enrique Coletti (941-952-8164)
4652 OAK HOLLOW DR #19, SARASOTA, FL 34241
$215,00038 Days on yellowkey MLS ID: A4696117
0 Days Off yellowkey (back on 6/28/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1679 Built: 1980Monthly Fee: $60 Tax: $2,291 (2025)Community: HammocksVilla
Taxes:$2,291
Elementary School: Lakeview Elementary
Middle School: Sarasota Middle
Remarks: Under contract-accepting backup offers. Rarely does a corner-unit villa with such an expansive yard become available. Offering a solid foundation and potential to make it your own, this 3 bedroom, 2 bath residence is located within Hammocks 1, a well-established subdivision in the gated community of Bent Tree that offers maintenance-free living with no age restrictions. With 1,679 square feet of living space, the home features a newer roof (2024), water heater (2023), and A/C system (2020), providing peace of mind for years to come. Offered furnished, this property presents a convenient opportunity for seasonal residents or year-round homeowners alike. The screened lanai provides the perfect setting for outdoor dining or enjoying a quiet morning coffee while taking in the peaceful natural surroundings. Frequent visits from birds and deer add to the charm of this unique homesite. Ideally positioned on a quiet, low-traffic street, this property enjoys one of the more desirable settings within Hammocks 1. Additional highlights include a two-car garage, indoor laundry, spacious primary suite with a walk-in closet, and beautifully tree-lined streets that add to the character of the community. Notably, the property is not located within a flood zone, offering added confidence for future owners. Conveniently located just minutes from everyday essentials, including Publix, Walmart, Home Depot, and University Town Center, with easy access to I-75 and a short drive to Sarasota's renowned beaches, dining, and entertainment. Opportunities to secure a corner-unit homesite with this much outdoor space in Bent Tree are few and far between. Schedule your showing today and discover why so many residents love living here.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Daniel Carrozzo (941-400-8462)
2545 BROWNING ST, SARASOTA, FL 34237
$699,00090 Days on yellowkey MLS ID: A4687679
REDUCED by $26,000 (3.6%) on 07/03/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1726 Built: 1958 Tax: $8,379 (2025)Community: Hudson ParkSingle Family
Taxes:$8,379
Middle School: Brookside Middle
Remarks: Welcome to this charming home in the conveniently located Alta Vista neighborhood, just minutes from Downtown Sarasota and the best the area has to offer. This move-in ready 3-bedroom, 2-bathroom home sits on a rare double lot on a quiet dead-end street, offering a spacious private backyard with plenty of room to relax, entertain, or expand. With no deed restrictions, you have the flexibility to make this property your own, including space for boat or RV parking. The fenced backyard provides added privacy and functionality, perfect for outdoor living. Inside, you’ll find an open split floor plan filled with natural light, creating a warm and inviting atmosphere. The home has been updated with new plumbing, a remodeled kitchen and bathrooms, and easy-maintenance flooring throughout. Additional features include pavers, modern finishes, and functional living spaces designed for comfort and convenience. The property may be sold furnished, making it a great option for a primary residence, seasonal use, or investment. The double lot also offers future possibilities for expansion or new construction. Enjoy being just a short walk to the Legacy Trail, along with close proximity to Downtown Sarasota, shopping, dining, and the beautiful beaches, including Siesta Key. Schedule your private showing today!
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Beverly Perez (941-323-4600)
105 TUCKER AVE, SARASOTA, FL 34232
$599,995168 Days on yellowkey MLS ID: A4680183
REDUCED by $25,005 (4.0%) on 05/26/2026
Bed: 3 Bath: 1.5 Gar: 2 Liv Area Sq Ft: 1562 Built: 1940 Tax: $4,798 (2025)Community: Tuckers SubSpa: YesSingle Family
Taxes:$4,798
Elementary School: Fruitville Elementary
Remarks: A rare opportunity to acquire a beautifully restored 1940 coastal-inspired Key West style Florida bungalow positioned on an oversized 0.38-acre parcel offering future subdivision potential. Following closing, the property may be split into three separate lots, creating one residence lot with the existing home, and two additional buildable parcels—an exceptional value-add opportunity in a highly desirable Sarasota location. The 3-bedroom, 1.5-bath residence blends architectural character with curated modern upgrades. Interior highlights include refinished bamboo and wood flooring, exposed wood ceiling beams, and custom cedar built-ins that enhance the home’s refined coastal Key West bungalow aesthetic. The chef’s kitchen is thoughtfully designed with solid wood cabinetry, quartz countertops, an imported Italian tile backsplash, and updated stainless steel appliances. An adjacent addition provides expanded pantry storage and a laundry area, leading to a spa-inspired primary bathroom featuring dual vanities, a freestanding soaking tub, and a walk-in rain shower. The upper level hosts a private primary suite with a generous walk-in closet with built-ins, a second bedroom, and an updated half bath, while the third bedroom is conveniently located on the main level—ideal for guest accommodations or flexible use. Outdoor living has been elevated to an almost resort-style experience, featuring a 12-foot above-ground pool/spa with custom wood decking, multiple patios finished with imported Italian crystal tile, and a lush botanical setting with over 200 plantings and mature fruit trees including banana, mango, avocado, peach, and guava. Additional amenities include a pavilion, private outdoor shower, and a firepit designed for elevated entertaining and relaxation. Significant capital improvements include a 2023 metal roof, hurricane-rated windows, 2021 HVAC system, 2022 water heater, recent connection to public water, and a 2024 well pump with filtration system also on property. The home offers insulated and drywalled interiors, newly installed wheelchair-accessible outdoor walkway paths, an extended 6+ vehicle driveway, and a 12x14 detached workshop or garage, further enhancing functional versatility. With no HOA, no deed restrictions, and no flood insurance required, this property presents an exceptional combination of lifestyle appeal and long-term investment flexibility. Ideally located just minutes from downtown Sarasota’s premier dining, shopping, and cultural attractions, this offering is well-suited for private ownership, redevelopment, or strategic portfolio expansion.
Listing is courtesy of: DREAMIFY REAL ESTATE LLC (941-827-0700)
Listing Agent: Michael Grant (941-800-8585)
2300 LINDSTROM ST, SARASOTA, FL 34237
$749,00034 Days on yellowkey MLS ID: A4693299
REDUCED by $30,000 (3.9%) on 07/06/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2084 Built: 2021Monthly Fee: $654 Tax: $9,853 (2025)Community: Payne Park Ph 1Townhouse
Taxes:$9,853
Middle School: Booker Middle
Remarks: One of the brightest units in Payne Park, this meticulously maintained 3 bedroom/3.5 Bath (2084 SF) modern coastal home presents in near-new condition, offers a setting rarely found in downtown Sarasota. This Malcolm model (Largest Payne Park Villa) is perfectly positioned on one of the best corners to allow for "light and air" on three sides of the unit. Views includes a West view of Payne Park (pond) and a Northeast view of the pool. Payne Park is located right on the Legacy Trail with this home delivering an elevated lifestyle where walkability, recreation, and vibrant city energy converge. The main living level is thoughtfully designed for everyday living and entertaining. The chef's kitchen is a standout, featuring floor-to-ceiling white wood cabinetry with crown molding and brass hardware finished with a white quartz countertop. Modern glass and brass pendant lighting complement the kitchen's centerpiece island, which provides additional seating and storage. A custom tile feature wall frames the apron sink, positioned beneath two large windows that flood the space with natural light. The adjacent dining area flows nicely into the family room showcases a wall of windows. A private balcony extends the living space and provides space to relax. On the lower level, Bedroom 2 can be configured as a home office and offers exceptional flexibility with a full bath and closet. This level also provides access to a spacious paver stone patio with iron fencing and a gated entrance, ideal for outdoor enjoyment. Completing this floor is a two-car garage. On the third floor, you will find a generous sized primary bedroom with a well-appointed en-suite bath that includes a dual sink vanity, large walk-in shower with glass enclosure and an oversized walk-in closet with built-in shelving. Bedroom 3 also includes its own en-suite bath, offering comfort and privacy for guests or family members. A convenient laundry closet completes this level. Impeccable location and value! Buyers and/or Buyers Agent to verify all pertinent information, including room sizes, as they may be approximate. All Association information should be verified with Property Management Company or Association. Information deemed reliable but not guaranteed.
Listing Agent: Robert Robinson (941-587-2739)
6234 MIDNIGHT PASS RD #307, SARASOTA, FL 34242
$1,100,00074 Days on yellowkey MLS ID: A4692040
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1105 Built: 1979 Tax: $9,703 (2025)Community: Siesta Dunes BeachCondo
Taxes:$9,703
Elementary School: Phillippi Shores Elementary
Remarks: Siesta Key offer this Two Bedroom, Two Bath home with Full Views of the Gulf of Mexico. Turnkey furnished. Carport and storage closet. Screened lanai. Weekly rental can give you extra income. Both bedrooms have walk-in closets. Impact windows. You can enjoy the beach chairs and lounges on the famous "White Sand Beach", Gulf front circular pool that is the centerpiece of the community. On-site management. This centrally located community is near shopping and restaurants. It is a short trolley ride to Siesta Key Village.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Marlene Marshall (941-539-8850)
6020 MIDNIGHT PASS RD #49, SARASOTA, FL 34242
$625,00012 Days on yellowkey MLS ID: A4698693
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 834 Built: 1964 Tax: $3,492 (2025)Community: Aloha Kai AptsCondo
Taxes:$3,492
Remarks: Turn-Key Furnished Villa in Aloha Kai – One of Siesta Key's Premier Beachfront Communities! Welcome to your island retreat just steps from world-famous Siesta Key Beach. This beautifully updated 2-bedroom, 1.5-bath villa offers the perfect combination of coastal living, investment potential, and resort-style amenities. Whether you're searching for a seasonal getaway, full-time residence, or income-producing property, this exceptional opportunity checks every box. Thoughtfully updated, the home features a newer metal roof (2020), impact-rated windows and front door, upgraded 200-amp electrical service, a 2023 water heater, and an updated kitchen with modern cabinetry, quality countertops, and newer appliances. Offered turn-key furnished, it's ready for immediate enjoyment or rental. The first floor experienced water intrusion during Hurricane Milton. Following the storm, the owners completed professional remediation, including a fully permitted renovation and independent mold testing with negative results. Documentation is available, providing confidence in the quality of the restoration. Nestled within the lush, tropical grounds of Aloha Kai, residents enjoy private deeded beach access to Siesta Key Beach, a heated Olympic-size swimming pool, clubhouse, shuffleboard courts, beautifully maintained landscaping, and on-site management. The community permits short-term rentals, making this an attractive opportunity for both personal enjoyment and investment income. Ideally located near Siesta Key Village, waterfront dining, shopping, boating, and all that Sarasota has to offer, this is your opportunity to own a move-in-ready beach villa in one of Florida's most desirable coastal communities. Buyer should verify all room dimensions, rental policies, and community regulations with the co-op association and management.
Listing Agent: Rex Glasson (941-587-6135)
2303 LOMA LINDA ST, SARASOTA, FL 34239
$1,850,000197 Days on yellowkey MLS ID: A4676235
2 Days Off yellowkey (back on 7/6/2026)
REDUCED by $49,000 (2.6%) on 06/24/2026
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
Remarks: Under contract-accepting backup offers. 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)
1824 WEBBER ST, SARASOTA, FL 34239
$650,00078 Days on yellowkey MLS ID: A4691535
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 1680 Built: 1968 Tax: $7,613 (2025)Community: Poinsettia Park 2Half Duplex
Taxes:$7,613
Elementary School: Southside Elementary
Remarks: Investor / Builder Alert! Exceptional WEST OF TRAIL opportunity in one of Sarasota’s desirable neighborhoods, Poinsettia Park. Located just steps from top-rated Southside Elementary School, this property offers incredible potential for redevelopment. The existing structure is a grandfathered duplex that is in very poor condition and best suited for teardown. The true value lies in the land — a 50’ x 118’ lot ideally positioned for a stunning new custom home. But if you prefer, you can keep it as a duplex and rent it. Consider it a blank canvas. Located within the city limits so short term rentals are acceptable. Enjoy a highly sought-after location just minutes to the shops and dining of Southside Village, the world-renowned beaches of Siesta Key, and the vibrant arts, dining, and waterfront lifestyle of Downtown Sarasota. Whether you’re a builder, investor, or end user looking to create a dream home, this is a rare chance to build new in an established, high-demand area surrounded by luxury properties. Opportunities like this are becoming increasingly scarce—don’t miss your chance to capitalize on this premium location! Sold as is with right to inspect.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Ryan Carson (941-685-2879)
565 COMMONWEALTH PL, SARASOTA, FL 34242
$1,895,00013 Days on yellowkey MLS ID: A4698496
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1849 Built: 1973Monthly Fee: $42 Tax: $14,976 (2025)Community: Siestas Bayside WatSpa: YesSingle Family
Taxes:$14,976
Remarks: Tucked away on a quiet cul-de-sac in one of Siesta Key's most desirable waterfront neighborhoods, this beautifully maintained canal-front residence offers the kind of island lifestyle buyers dream about. Set on an exceptional pie-shaped homesite with 129 feet of waterfront and recapped seawall, this low-wake arm of the Grand Canal offers quick access to Roberts Bay while its calm, protected basin provides a peaceful, private setting for both boating and everyday waterfront living. Designed for easy indoor-outdoor living, the three-bedroom, two-bath home opens seamlessly to a private backyard retreat where a heated pool, fire pit and spacious screened lanai invite long afternoons in the Florida sunshine and evenings spent under the palms. The broad canal views create an unexpected sense of space, offering peaceful water vistas without feeling confined by neighboring homes. Whether entertaining friends or enjoying a quiet morning overlooking the water, every space feels relaxed, comfortable and unmistakably coastal. Inside, tray ceilings, plantation shutters and an abundance of natural light create a warm, welcoming atmosphere. The thoughtfully updated kitchen features solid maple cabinetry, granite countertops, premium appliances, abundant storage and a convenient pass-through window for effortless entertaining. The spacious primary suite overlooks the pool and canal, complete with a generous walk-in closet and an updated ensuite bath with dual vanities, soaking tub and separate shower. A split-bedroom floor plan offers privacy for owners and guests alike. Boaters will appreciate the Trex dock, expanded waterside paver patio, 10,000-pound lift, fish cleaning station and protected canal setting, while the fully fenced yard, hurricane shutters, oversized laundry room, paver driveway and two-car garage add everyday convenience. The home remained dry during the 2024 storms, offering valuable peace of mind. Perhaps what makes this property so special isn't simply its long list of amenities, but the life it invites. It's the kind of home where grandchildren cannonball into the pool, dogs race across the backyard, friends linger around the fire pit long after sunset, and an evening boat ride becomes part of the daily routine. For those ready to trade elevators and HOA hallways for a private dock, a backyard made for gathering and a different sense of home, this is a rare opportunity. Just minutes from our famous Siesta Beach, the lively Siesta Key Village and the vibrancy downtown Sarasota, it offers waterfront living that feels both peaceful and connected.
Listing Agent: Rudy Dudon (941-234-3991)
206 HOURGLASS WAY #V10, SARASOTA, FL 34242
$625,00066 Days on yellowkey MLS ID: A4690141
REDUCED by $15,000 (2.3%) on 07/06/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1462 Built: 1968Monthly Fee: $1,793 Tax: $5,579 (2025)Community: Whispering SandsVilla
Taxes:$5,579
Remarks: Welcome to your coastal retreat in the form of this secluded, 2 bed/2 bath freestanding villa with one car garage in the premiere GULF FRONT property of Whispering Sands. OFFERED FURNISHED. This surprisingly large, 1,462 square foot property has been UPDATED in 2025 with fresh paint, NEW crown molding & baseboards, NEW kitchen and updated baths. The exceptionally large living room allows for multiple seating groups, while a wall of floor to ceiling sliders – treated with beautiful shades - provides an abundance of natural light. Meal prep is easy in your bright NEW kitchen featuring white cabinetry, subway tile backsplash, granite counters, stainless Whirlpool appliances, recessed lighting, fandelier, & vinyl plank flooring. Three sets of new hurricane impact sliders open from the kitchen, dining room, and 2nd bedroom into your private fenced brick paver patio which offers valuable outdoor space for sunny relaxation or effortless entertaining. Both newly carpeted bedrooms feature an extended living space to accommodate a small seating group, desk, or exercise equipment. The bathrooms have been refreshed with NEW granite countertops, cabinets, vanities & fixtures. NEW 2026 stacked W/D in garage. 2019 HVAC. Recent enhancements include exterior pressure washing and villa painting in February 2026. Newly updated brick paver driveway. New landscaping is being planned by the HOA starting in 2026. Whispering Sands is a premiere 55+ Gulf front property ideally located next to the colorful boutiques and dining options of Siesta Key Village, and offers 800’ of PRIVATE beach, 2 heated pools, new beachside Tiki Hut, grills, shuffleboard, canoe/kayak storage, security, & onsite management. The clubhouse is scheduled to be remodeled in 2026 and when completed will include fitness rooms, catering kitchen, and an elegant and comfortable space for social gatherings. Seller is willing to include 3 year new Kia SUV automobile with acceptable offer. Your coastal retreat awaits!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Harriet Stopher (404-316-8944)
1157 WESTWAY DR, SARASOTA, FL 34236
$14,900,00012 Days on yellowkey MLS ID: A4696910
Bed: 6 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 9162 Built: 1974Monthly Fee: $42 Tax: $70,635 (2025)Community: Lido CSpa: NoSingle Family
Taxes:$70,635
Remarks: Some properties tell the story of Sarasota's evolution. Offered for the first time publicly in half a century, this waterfront estate in Lido Shores presents a rare opportunity to become the next steward of 1.34 acres with 247 feet of western shoreline. Held by only two families since 1974, both recognized for their lasting contributions to the Sarasota community, the property offers a unique connection to the people and vision that helped shape the city we know today. A rare slice of Sarasota's legacy is now ready for its next chapter. Designed by Seibert Architects, the residence reflects an important chapter in Sarasota's architectural heritage. The home encompasses more than 9,000 square feet with six bedrooms and six baths, including a library and billiards room. This home was thoughtfully designed to embrace its waterfront setting through expansive living spaces, gathering areas and water views throughout, including multiple terraces. The generous homesite presents exceptional possibilities for restoration, renovation or the creation of a new waterfront estate. Opportunities offering this scale of western-facing water frontage, private beach access and architectural provenance are increasingly rare along Sarasota's coastline. Offering a remarkable sense of privacy, yet just minutes from the boutiques and fine dining of St. Armands Circle, downtown Sarasota's renowned arts and cultural institutions, theaters, galleries and museums, this exceptional property also enjoys convenient access to international airports and multiple international gateways, connecting this storied waterfront setting to destinations around the world.
Listing Agent: Melodie Palmer (941-539-4046)
1800 BENJAMIN FRANKLIN DR #A905, SARASOTA, FL 34236
$1,455,00074 Days on yellowkey MLS ID: A4692060
1 Days Off yellowkey (back on 7/6/2026)
REDUCED by $45,000 (3.0%) on 06/08/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1350 Built: 1996 Tax: $19,414 (2025)Community: L Elegance On Lido BeachSpa: YesCondo
Taxes:$19,414
Remarks: Under contract-accepting backup offers. Direct Gulf-front views from the living room and both bedrooms. Newly widened beach. Ninth-floor elevation. Wake to the sound of waves and unobstructed Gulf views from this ninth-floor residence at L’Elegance on Lido Beach, where the living room, primary suite, and guest bedroom all enjoy direct Gulf frontage—a rarely available opportunity on Lido Beach. Positioned directly on the beach, this residence features an expansive Gulf-front terrace designed for year-round sunsets, coastal breezes, and panoramic water views stretching across the horizon. Residents of L’Elegance enjoy an exceptional collection of amenities including a 24-hour guarded entrance, Gulf-front resort-style pool and spa, updated fitness center, tennis courts, clubhouse, and a private deeded beach reserved exclusively for residents and their guests—offering a more peaceful and secluded beachfront experience. Adding to its appeal, Sarasota County’s recent beach renourishment has dramatically expanded the shoreline, creating an even more impressive beachfront setting and enhancing the enjoyment of this coveted stretch of Lido Key and the community’s private deeded beach. Located on the coveted south end of Lido Key, residents enjoy a quieter beachfront setting while remaining just moments from the boutiques, restaurants, and waterfront dining of St. Armands Circle, as well as the arts, entertainment, and cultural attractions of downtown Sarasota. Whether envisioned as a seasonal escape or a full-time coastal residence, this offering presents a rare opportunity to own direct Gulf-front property on one of Sarasota’s most desirable beaches—where every day begins with sweeping water views and ends with Sarasota’s unforgettable sunsets.
Listing Agent: Lisa Garcia (941-266-9060)
435 S GULFSTREAM AVE #605, SARASOTA, FL 34236
$429,000106 Days on yellowkey MLS ID: A4688025
REDUCED by $15,900 (3.6%) on 07/06/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1537 Built: 1972 Tax: $6,289 (2025)Community: Regency HouseSpa: NoCondo
Taxes:$6,289
Remarks: One or more photo(s) has been virtually staged. Welcome to The Regency House and to the 'gold coast of Sarasota' directly on Sarasota Bay! Priced at the lowest price per square foot in the downtown bayfront district and beyond and just reduced AGAIN! This unit is on the sixth floor and looks over the city and Palm Avenue. This condo is ready for your rehab and waiting for your own touches! Features include a brand-new A/C system, huge great room looking out to a sliding glass-enclosed lanai facing north with a peek view of Island Park and Sarasota Bay! This has a split bedroom floor plan and both bedrooms are ensuite. The primary bedroom closet is massive and there is an inside utility closet for storage or even reconfigure into a small office. There are several different views from the windows in the many rooms because of the building's unique floor plan and design! The Regency House features a 24/7 onsite concierge attendant, a library nook, club room with kitchen, small fitness center, and a heated swimming pool that is about to be totally transformed and expanded with added grill area and covered gazebo. One covered carport space is included on rotation. The Regency House sits proudly across Tamiami Trail from the Sarasota bayfront with O'Leary's and Marina Jack Restaurants and marina and Island Park. Fabulous Selby Gardens is a short distance away as are many delightful culinary experiences and shopping up and down popular Palm Avenue. Enjoy the area arts including Florida Studio Theatre-all within seconds to minutes. Come make this huge downtown condo how you want it in a very well-run condominium complex!
Listing Agent: Joe Cleary (941-650-8485)
3631 SAN REMO TER, SARASOTA, FL 34239
$7,995,000253 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
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.
Listing Agent: Joel Schemmel (941-587-4894)
521 CUMMINGS ST, SARASOTA, FL 34242
$1,450,00010 Days on yellowkey MLS ID: A4696604
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2500 Built: 1983 Tax: $7,154 (2025)Community: Ocean Beach RepSingle Family
Taxes:$7,154
Remarks: Tucked away on a quiet cul-de-sac on north Siesta Key, this Key West-inspired canal-front retreat captures the ease of casual island living with boating water, inviting outdoor spaces and easy access to Siesta Village, the famous white quartz sands of Siesta Beach and the azure waters of the Gulf. Set along 95 feet of private canal frontage just off the Grand Canal, the property offers a dock, a covered 5,000-pound boat lift and direct access to the Intracoastal Waterway, creating an ideal setting for those who want to enjoy the water from their own backyard. Designed for effortless indoor-outdoor living, the home features an expansive elevated deck and contemporary cable railings overlooking the canal and surrounding natural scenery, a heated pool with a cascading stone waterfall, a covered bar area and a fenced, low-maintenance yard surrounded by tropical landscaping. Whether hosting friends, relaxing after a day on the boat or enjoying the island breeze, the outdoor areas offer a private, versatile setting for everyday enjoyment. Inside, vaulted ceilings, a neutral palette and an open-concept layout create a light, comfortable atmosphere. The kitchen is positioned at the heart of the home and features granite countertops, stainless steel appliances, dual sinks, a center island with a JennAir cooktop and a breakfast bar that connects easily to the main living and dining areas. A wood-burning fireplace adds warmth and character to the gathering space. The primary suite offers a peaceful retreat with sliding glass doors opening to a screened lanai, along with an en-suite bath featuring dual vanities, a walk-in shower and a charming window seat. Two additional bedrooms are thoughtfully positioned in their own wing with a full bath and convenient laundry room nearby. Additional features include impact glass on most openings, hurricane-rated doors, metal roof, Nichiha siding, Trex decking, cable railings, two garages and a full pool bath, bonus room and storage area on the ground level. Positioned at one of the highest elevations on the street, the home offers added peace of mind in storm season. Just a short distance from Siesta Key’s renowned beaches, vibrant Village dining, boutiques and nightlife, this move-in-ready waterfront home offers exceptional flexibility as a full-time residence, seasonal getaway or investment opportunity in one of Sarasota’s most beloved island communities. Close to the Out-of-Door Academy’s lower school and only 15 minutes by car to vibrant downtown Sarasota’s restaurants, shopping and entertainment.
Listing Agent: Judie Berger (941-928-3424)
471 ISLAND CIR, SARASOTA, FL 34242
$2,100,0009 Days on yellowkey MLS ID: A4698115
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2922 Built: 2014 Tax: $13,929 (2025)Community: Sarasota BeachSingle Family
Taxes:$13,929
Remarks: Offered for the first time, 471 Island Circle is a private contemporary coastal retreat designed for modern luxury, effortless living and the ease of a low-maintenance Siesta Key lifestyle. Ideally positioned in the community of Palm Island, close to Siesta Beach and the charm of Siesta Village, this three-level residence offers a rare blend of privacy, quality construction and everyday comfort in one of the island’s most desirable settings. From the gated entry and walled-courtyard approach to the private pool area, the home feels wonderfully tucked away while remaining moments from the beach, boutiques, dining and the relaxed energy that makes Siesta Key so loved. Built by MGB (My Green Building) with a focus on strength, efficiency and peace of mind, the residence features solid concrete block construction, reinforced with rebar and poured concrete tied to the roof structure, impact-rated materials and a low-maintenance exterior. It is an ideal lock-and-leave island home for those who want to enjoy the beauty of coastal living without the demands of a more traditional high-maintenance property. Inside, a striking floating steel staircase with stainless steel cable detailing creates a memorable first impression, while the elevator provides easy access to all levels. The upper main living level is filled with natural light, with open dining and family spaces designed for comfortable everyday living and easy entertaining. The sleek Cucina Ricci kitchen features abundant contemporary cabinetry, quartz countertops and premium Thermador appliances, including dual ovens, an icemaker, a five-burner induction cooktop, a concealed refrigerator and wine refrigeration. A cleverly designed hidden television rotates to be viewed from both the kitchen and living areas. Just beyond, a large west-facing balcony extends the living space outdoors and offers a beautiful setting for open-air dining, sunset cocktails and evening breezes. A stylish half bath completes the main living level. The second floor offers three en suite bedrooms, each thoughtfully designed with privacy and comfort in mind. Contemporary baths feature striking tile selections, floating vanities and clean modern finishes. An additional balcony overlooks the private courtyard pool below, creating a quiet connection between the interiors and outdoor living spaces. A convenient laundry room is located nearby. Outdoors, the walled pool courtyard is designed for privacy, sunning, swimming and relaxed coastal enjoyment, offering the feel of a private resort with minimal upkeep. Additional features include two-zone air conditioning for enhanced efficiency, generous storage and a two-car tandem garage. From morning at the beach to evenings near the Village or sunset views from your own balcony, every day here feels like a vacation. When you are ready to explore beyond the island, vibrant downtown Sarasota is just a short drive away, offering world-class dining, arts and culture and entertainment.
2442 WOOD ST, SARASOTA, FL 34237
$449,000180 Days on yellowkey MLS ID: A4678152
REDUCED by $23,000 (4.9%) on 05/28/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1279 Built: 1951 Tax: $5,715 (2025)Community: Hudson ParkSingle Family
Taxes:$5,715
Remarks: Live in one of Sarasota’s most desirable neighborhoods! Priced to sell. This charming home offers two generously sized bedrooms plus a versatile third space that can serve as a sunroom, office, or private in-law suite/studio. This additional area includes its own bathroom, kitchenette, closet, and separate rear entrance—perfect for guests or rental potential. Inside, you’ll find a cozy layout with a welcoming kitchen nook and comfortable living area, ideal for relaxing and unwinding. The home has been thoughtfully updated with a remodeled kitchen, a newer roof (2018), granite vanity top and sink with brushed nickel fixtures (2020), a brand-new water heater (2025), upgraded lighting (2025), and numerous additional improvements throughout. Enjoy your morning coffee on the inviting front porch or entertain and relax on the back patio. The backyard features a two-car carport, storage sheds, and a newly completed, eye-catching stone fence that adds both ambiance and privacy. Conveniently located just minutes from downtown Sarasota, shopping, dining, and the world-famous Siesta Key Beach, as well as other nearby beaches, this home offers both comfort and accessibility. Additional highlights include RV parking and multi-family zoning, providing excellent flexibility and investment potential. Schedule your private showing today and experience everything this beautiful home has to offer!
Listing is courtesy of: CHROME REALTY LLC (941-363-6300)
Listing Agent: Marni Hayden (941-809-5044)
2120 CRAFT LN, SARASOTA, FL 34239
$699,00036 Days on yellowkey MLS ID: A4696329
REDUCED by $50,000 (6.7%) on 06/22/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1570 Built: 1956Monthly Fee: $17 Tax: $6,826 (2025)Community: Norwood ParkSingle Family
Taxes:$6,826
Remarks: Under contract-accepting backup offers. Beautifully remodeled coastal cottage in one of Sarasota’s most coveted locations—just minutes to Siesta Key, downtown Sarasota, and steps from Arlington Park and in the sought after Southside School District. Completely renovated late 2024, this move-in ready residence offers peace of mind with a substantial plumbing upgrade (37K) -with full repipe of all cast iron and all new hot and cold water lines. Additional all new IMPACT windows, beautiful new tile flooring throughout, and a fully transformed kitchen designed to impress. WOW that kitchen!! Quartz countertops, stylish cabinetry, designer lighting and backsplash, and effortless flow into the living spaces, the kitchen serves as the true heart of the home—perfect for everyday living and entertaining alike. All new appliances. Warm honey-toned wood-look tile creates a seamless, elevated feel throughout, while the desirable split floor plan offers both comfort and privacy. Tucked away from the guest bedrooms, the spacious primary suite feels like a private retreat and offers a rare feature for a home of this era—a generously sized closet along with a beautifully updated ensuite bath. Additional bedrooms provide flexibility for guests, family, or a stylish home office, including one space ideal for built-in workspace potential. The bright, welcoming living area invites relaxation, while the peaceful lanai, shaded beneath mature trees, creates the perfect backdrop for morning coffee, evening cocktails, or unwinding after a day at the beach. And then there is the location—truly exceptional. Just minutes to the world-famous Siesta Key, vibrant downtown Sarasota, waterfront dining, boutique shopping, arts, and entertainment. Even better, Arlington Park is only moments away, offering pools, pickleball, tennis courts, walking trails, playgrounds, and lush green space right in your neighborhood. Whether you are seeking a full-time residence, winter retreat, or investment opportunity, this home delivers the quintessential Sarasota lifestyle with style, convenience, and coastal charm.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Danelle Haag (941-806-9821)
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