Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
3631 SAN REMO TER, SARASOTA, FL 34239
$7,995,000222 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$68,556
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
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 is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
5500 MERRIMAC DR, SARASOTA, FL 34231
$1,685,000101 Days on yellowkey MLS ID: A4684914
REDUCED by $85,000 (4.8%) on 04/17/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2790 Built: 1974 Tax: $6,537 (2025)Community: Phillippi Gardens 08Spa: YesSingle Family
Taxes:$6,537
Elementary School: Phillippi Shores Elementary
High School: Riverview High
Remarks: Live the Ultimate Florida Lifestyle in This Waterfront Paradise! Nestled in the heart of Phillippi Gardens, this extraordinary property offers the perfect blend of tranquility, luxury, and convenience. Set on an OVERSIZED .61-ACRE LOT WITH OVER 400 FEET OF PRIVATE WATER FRONTAGE. Along two serene waterways just off Phillippi Creek, this home is a true tropical oasis—peaceful and secluded, yet minutes from everything Sarasota has to offer. Inside, the residence showcases a flexible layout with FOUR SPACIOUS BEDROOMS, some easily adaptable for office, studio, or guest use, and FOUR FULL BATHROOMS making it ideal for hosting loved ones and guests. The interior has been thoughtfully updated from 2017 through 2024 blending modern comfort with timeless charm. Interior Highlights Include: An expansive great room with a DUAL-SIDED WOOD-BURNING FIREPLACE, a gourmet kitchen featuring stainless steel appliances, farmhouse sink and pot filler. Three bedrooms on the main level, including one en-suite, and a second-floor master suite with a PRIVATE BALCONY OFFERING BREATHTAKING SUNRISE AND SUNSET VIEWS. Step outside and feel like you're on vacation every day. The lush, tropical grounds are packed with resort-style amenities: Tiki hut with a full bar and grill, two fire pits, five-zone low-voltage night lighting creating a magical evening ambiance, heated pool and spa, boat lift, a new boathouse (2019) and new seawall (2023/2024). Additional Upgrades: Two new A/C units (2019), septic-to-sewer conversion (2018). Tucked away at the end of a quiet cul-de-sac, this home offers privacy without sacrificing accessibility. You're just a short bike ride to the Gulf beaches, near The Landings for shopping and dining, and minutes from downtown Sarasota’s vibrant arts and culture scene.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Steve Abbe (941-400-3969)
2475 BAY ST, SARASOTA, FL 34237
$2,012,000124 Days on yellowkey MLS ID: A4676732
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2874 Built: 2024 Tax: $14,004 (2025)Community: Hudson ParkSingle Family
Taxes:$14,004
Elementary School: Alta Vista Elementary
Remarks: Experience refined modern living at 2475 Bay Street, a brand-new contemporary residence offering 2,874 square feet of thoughtfully designed space. Clean architectural lines and a striking façade set the tone, while inside, sun-filled interiors reveal soaring ceilings, expansive open-concept living areas, and walls of glass that create a seamless indoor-outdoor connection. The home is designed to feel both elevated and livable, with spaces that flow naturally for entertaining, relaxing, and everyday life. The home features four bedrooms and four bathrooms, including a main-level primary suite that offers split-plan privacy and direct access to the pool area. The primary bath includes a double vanity, walk-in shower, soaking tub, and spacious his-and-hers closets with built-in accessories. The chef’s kitchen is outfitted with Café appliances accented in gold, premium cabinetry, Calcutta quartz countertops throughout the home, and a dramatic waterfall island seating eight. An upstairs living area overlooks the main level and opens to a second-story balcony, while additional bedrooms feature en-suite baths for comfort and privacy. Additional highlights include a custom resort-style pool, fully fenced yard, covered lanai with a fully equipped outdoor kitchen, two-car garage, energy-efficient construction, paver driveway accommodating up to four vehicles, and a mudroom with direct access to the pantry. Ideally located in central Sarasota, this home offers a peaceful residential setting with quick access to downtown and the area’s top attractions. Enjoy nearby Main Street dining, boutique shopping, and cultural venues such as the Sarasota Opera House, Florida Studio Theatre, and McCurdy’s Comedy Theatre. Outdoor and lifestyle destinations include Bayfront Park and Marina, Marie Selby Botanical Gardens, Payne Park, St. Armands Circle, Sarasota Jungle Gardens, The John and Mable Ringling Museum of Art, and Mote Marine Aquarium. World-renowned beaches including Siesta Key, Lido Key, and Longboat Key are just minutes away, along with convenient access to Publix, Sarasota Memorial Hospital, top schools, and Sarasota-Bradenton International Airport. Schedule your private tour and experience the design, flow, and lifestyle of this unique Sarasota property before it slips away.
Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)
Listing Agent: Desiree Doggett (941-900-6380)
1760 ARLINGTON ST, SARASOTA, FL 34239
$2,150,000303 Days on yellowkey MLS ID: A4661996
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2745 Built: 2012 Tax: $21,270 (2024)Community: Nichols Sarasota HeightsSpa: NoSingle Family
Taxes:$21,270
Tax Year: 2024
Remarks: One or more photo(s) has been virtually staged. Ideally positioned in Sarasota’s desired West of Trail, this 2012 custom-built three-bedroom, four-bath home blends timeless architecture with modern comfort—just a short stroll to Southside Village’s boutiques and cafés, Selby Gardens, the bay front, and Sarasota Memorial Hospital. Set on a fully fenced, 1/3-acre lot in the sought-after Southside Elementary district, the property offers a private oasis with a sun-soaked southern-exposure backyard—ideal for all-day light on the pool and covered patio. Outdoor living shines with a heated pool featuring a sun shelf, fire pit, landscaped lawn, and inviting front and back porches designed for effortless entertaining. Inside, nearly 2,800 square feet unfolds with a wood-burning fireplace, tile and luxury vinyl plank flooring, and a flexible layout suited for today’s lifestyle including a den/office that can easily be used as a fourth bedroom. The oversized laundry/mudroom streamlines daily life, while the two-car garage with extra storage adds convenience. The spacious primary suite opens directly to the pool and features dual walk-in closets and bath with double vanities, a walk-in shower, and soaking tub. Built with quality in mind—including block construction and a durable metal roof—this home offers peace of mind and enduring value. A rare opportunity to own newer construction West of Trail with accessibility, abundant natural light, and room to live the Sarasota lifestyle to its fullest—just minutes from downtown.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Katy Mcbrayer (941-400-2406)
251 SOUTHWINDS DR, SARASOTA, FL 34231
$149,500232 Days on yellowkey MLS ID: A4669553
REDUCED by $10,400 (6.5%) on 04/21/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 624 Built: 1963Monthly Fee: $195 Tax: $1,434 (2024)Community: South Winds Mhp Co-OpMobile Home
Taxes:$1,434
Remarks: Want to live near Siesta Key without breaking the bank? Here is your opportunity, in one of the most desirable 55+ co-op communities, South Winds! And for only $195/month for HOA fees, you get to enjoy maintenance free living in a friendly and active neighborhood with a heated pool, shuffleboard, bocce, pickleball, horseshoes, a putting green, library and recreation hall and more! The home features newly screened in lanai's on both sides, an attached storage shed and an oversized lot, one of the best in the entire community with green space in the front, a garden area in the back, and just a short distance to all amenities. The bathroom is also recently remodeled with granite counter, and a new walk in shower. AC new in 2020, and the home was re-piped in 2022. There is also a termite warranty and contract that conveys to the new owner! Here is your opportunity to live just 5 minutes to Siesta Key and 10 minutes to downtown Sarasota. Gulf Gate is also just 5 minutes away for amazing local restaurants and entertainment.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Adrian Mociran (941-302-8603)
1678 STARLING DR #102, SARASOTA, FL 34231
$305,000145 Days on yellowkey MLS ID: A4678531
REDUCED by $20,000 (6.2%) on 04/21/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1712 Built: 1989Monthly Fee: $167 Tax: $4,077 (2025)Community: Landings South Vii, The LandingsCondo
Taxes:$4,077
Remarks: One or more photo(s) has been virtually staged. Come live the Landings lifestyle. A sleek clean design awaits you in this first floor two bedroom, two bath condominium. An open plan with consistent flooring throughout and a neutral color pallet. A contemporary styled kitchen with white cabinetry, sleek black granite, white subway tile backsplash, and a stainless-steel appliance package. The primary bedroom is oversized with ample space for an office or exercise area. The ensuite bathroom has also enjoyed a makeover with travertine flooring and shower surround, dual sinks, the kitchen aesthetic has been repeated with clean white cabinetry and black granite. The guest bath has also been upgraded with new vanity, countertop, and sink. A private patio overlooking lush greenery is accessible via sliders from the eat-in kitchen and/or great room. A single car garage, opportunity for a larger pet, and immediate rental options are features of Landings South VII. Should you be looking to find a community where you can meet people-look no further than the Landings Racquet Club with eight har-tru tennis courts, heated pool and spa, exercise room, and activities for all occasions. The social calendar keeps members busy and is a great place to make friends. The Landings also has a nature Trail leading to a fishing pier/gazebo with storage area for kayaks. The Landings, a gated neighborhood located “west of the trail” is truly unique with its proximity to the revitalized Landings Shopping Center, Siesta Key, and downtown Sarasota.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Judy Greene (941-350-0451)
9393 MIDNIGHT PASS RD #P4, SARASOTA, FL 34242
$659,000226 Days on yellowkey MLS ID: A4669033
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1380 Built: 1975 Tax: $7,483 (2024)Community: Pointe On Midnight PassCondo
Taxes:$7,483
Remarks: Price Reduction!! ENJOY AWE-INSPIRING SUNRISES AND SUNSETS from this stunning two bedroom, two bath PENTHOUSE condo at the southernmost end of Siesta Key. A corner unit with extra windows, enjoy water views from every room! Wake to breath-taking sunrises over Neville Preserve on Little Sarasota Bay and marvel at spectacular sunsets over the Gulf of Mexico. The largest of units offered at The Pointe, this 10th floor residence is filled with natural light through abundant windows and sliding glass doors. The large kitchen opens to the living room which features beautiful engineered hardwood flooring, crown and base molding, and ceiling beams to separate the dining and living areas. A generous screened and glassed lanai - accessible from both the living room and the primary suite - provides your front-row seat to sunrises, downtown Sarasota, and spectacular wildlife. The private primary retreat offers a large bedroom, a walk-in closet, a built-in vanity with sink, and an ensuite bath with walk-in shower, second sink and toilet. A comfortable guest bedroom and full hall bath complete the main living space. A large laundry room with ample cabinetry, a walk-in utility room off the lanai and a large ground floor assigned lock-off bin provide coveted storage space. An oversized under-building parking space convenient to the building entry completes this unit. Located at the southern tip of Siesta Key, this 5+ acre gated community is beautifully landscaped and features every amenity: heated pool and spa, lighted tennis and pickle ball courts, private boat docks, kayak and canoe racks and launch, a beautiful and fully equipped club house, saunas, fitness centers, an island pavilion with grills, and on-site management and maintenance. A walkway along the water surrounding the property is idyllic for scenic strolls. The Pointe is just minutes' walk to Turtle Beach and three great restaurants. This really is a must see!
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Robert Ruiz (941-544-3299)
3209 ASHTON RD, SARASOTA, FL 34231
$599,00057 Days on yellowkey MLS ID: A4690471
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1586 Built: 1975 Tax: $5,588 (2025)Community: Ashton ParkSpa: YesSingle Family
Taxes:$5,588
Elementary School: Wilkinson Elementary
Remarks: Location, location, location! This 3-bedroom, 2-bath home with a bonus room sits on a desirable corner lot just 4 miles from world-renowned Siesta Key Beach. Ideally positioned minutes from downtown Sarasota and I-75, this property offers both convenience and lifestyle. Offered turnkey, this home is move-in ready and ideal as a primary residence, seasonal getaway, or investment opportunity. Inside, enjoy a split floorplan with comfortable living spaces, plus a versatile bonus room perfect for a home office, gym, or flex space. Recent updates include a 2020 A/C, along with a brand-new pool and spa, creating a private backyard retreat. The screened lanai overlooks the spacious yard, ideal for relaxing or entertaining. Additional features include a covered carport and under-roof storage. Located near top-rated A schools and just moments from shopping and dining at Gulf Gate Village. Outdoor enthusiasts will love being at the end of the street from Red Bug Slough Preserve, a 72-acre nature preserve with walking trails, picnic areas, and scenic Florida wildlife. No HOA fees. No CDD fees. A rare opportunity to own in a prime Sarasota location.
Listing is courtesy of: HARRY ROBBINS ASSOC INC (941-924-8346)
Listing Agent: Marlin Yoder (941-893-7406)
2823 MARSHALL DR, SARASOTA, FL 34239
$1,199,00057 Days on yellowkey MLS ID: A4690497
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1856 Built: 2020 Tax: $8,242 (2025)Community: Orange ParkSpa: YesSingle Family
Taxes:$8,242
Remarks: This stunning one-story custom-built home, completed in 2020, offers the ideal blend of modern design, high-quality construction and an unbeatable location. In the sought-after Southside Elementary School district, this three-bedroom, three-bath residence plus dedicated office is just minutes from Siesta Key, downtown Sarasota and Sarasota Memorial Hospital, placing you at the heart of everything that makes Sarasota exceptional. Designed for comfort and style, this home features a seamless open floor plan with soaring ceilings, corner pocket doors in the office and abundant natural light. The spacious kitchen is a chef’s dream, boasting quartz countertops, an oversized island, custom cabinetry and top-tier appliances. The smoky mirror wall at the entryway and built-in bookshelves add unique character, while recessed LED lighting enhances the contemporary ambiance. Go outside through the expansive sliding glass doors to your private backyard retreat. The pool and spa are surrounded by lush traveler palms, creating a serene, tropical escape. The fully fenced-in yard and generous patio space make this the ideal setting for entertaining or unwinding in privacy. Additional highlights include solid block construction, hurricane/impact-rated windows and doors, a two-car garage with additional driveway parking and a paver driveway for an elegant touch. With no HOA or CDD fees, this move-in-ready home offers the rare opportunity to experience luxury living in one of Sarasota’s desirable neighborhoods. Schedule your private tour today!
858 HUDSON AVE #858, SARASOTA, FL 34236
$920,000317 Days on yellowkey MLS ID: A4659647
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1533 Built: 1989 Tax: $11,352 (2024)Community: Hudson LandingsCondo
Taxes:$11,352
Remarks: Live the Downtown Waterfront Lifestyle – Deeded Dock Included! Brand new exterior paint! This beautifully renovated 2-bed, 2-bath condo with a den (optional 3rd bedroom) is a rare find in Sarasota’s desirable West of the Trail neighborhood. Located in Hudson Landings, a quiet 12-residence community just minutes from downtown and the bay, this light-filled second-floor corner unit offers modern updates and an unbeatable lifestyle. The list price includes a deeded dock and a 10,000-lb boat lift—brand new with updated pilings and cradle—providing quick, direct access to Sarasota Bay and the Gulf of Mexico. Bring your boat and enjoy the ultimate Florida living experience! Inside, you'll find a vaulted exposed-beam ceilings and abundant natural light with a sleek contemporary kitchen with custom cabinetry, newer granite countertops, glass tile backsplash, and top-of-the-line stainless steel appliances, including a built-in double oven and glass cooktop, and a spacious Italian-style shower in the updated bathrooms. Plus a cozy wood-burning fireplace for cool evenings and an enclosed patio with large hurricane-rated sliding windows, creating a bright and inviting dining area Step outside and you’re just a short walk to Marie Selby Botanical Gardens, the Sarasota Bayfront, and vibrant downtown Sarasota. This peaceful community also features a heated pool, lush landscaping, and a truly secluded atmosphere—no damage from recent storms Helene or Milton; docks and boats remained intact.
Listing is courtesy of: YORKSHIRE INTERNATIONAL R.E. (941-366-0000)
Listing Agent: Jules Roman (941-366-0000)
3619 PEMBROOK DR, SARASOTA, FL 34239
$585,000127 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
Taxes:$3,937
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)
1690 ASSISI DR #12, SARASOTA, FL 34231
$1,779,00058 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
$499,00078 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)
1250 N PORTOFINO DR #304, SARASOTA, FL 34242
$428,000421 Days on yellowkey MLS ID: A4649477
REDUCED by $10,000 (2.3%) on 04/15/2026
Bed: 1 Bath: 2.0 Liv Area Sq Ft: 780 Built: 1969 Tax: $3,898 (2024)Community: Siesta Harbor IiCondo
Taxes:$3,898
Remarks: Looking for a home for your boat, a beach lifestyle, or an investment? Enjoy sunrises over the marina, afternoons on Siesta Key Beach, and evenings on your enclosed balcony overlooking the boats and colorful skies. This furnished 1BR/2BA condo in Siesta Harbor is beautifully updated with an open floor plan, luxury vinyl flooring, remodeled kitchen (2022) with white shaker cabinetry, granite counters, glass backsplash, peninsula seating, and stainless appliances. Bathrooms feature quartz vanities and tiled showers; guest bath includes a soaking tub. Impact windows, same-floor laundry, and private storage add convenience. Siesta Harbor, a 55+ community, offers private beach access, heated pool/spa, lush landscaping, fishing pier, and a full calendar of social activities. Dock leases may be available for boats up to 30’. Additional amenities include covered parking, on-site manager, and a new roof (2025). Ideally located off the South Bridge near dining, shops, and the free Siesta Key trolley, this turnkey condo is perfect as a vacation retreat, full-time residence, or investment.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Marci Mcfarland (941-961-3390)
6334 MIDNIGHT PASS RD #41, SARASOTA, FL 34242
$629,00067 Days on yellowkey MLS ID: A4688750
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 612 Built: 1962 Tax: $3,759 (2025)Community: Siesta RoyaleSpa: NoCondo
Taxes:$3,759
Remarks: Siesta Royale is a Beachfront complex on Siesta Key located on the world famous Crescent Beach. This unit is Located right by the pool and close to the beach. This unit has been updated with High end laminant flooring throughout, new appiances, Granite counters and all new impact windows with beautiful finishing touches that makes you feel like you are really on vacation. Perfect for investment or full time use, Parking right outside unit, No stairs. This complex is close to many retaurants, boating, parasailng and shopping. This unit has a good rental histoy with steady rentals though out the year. Dont miss this one.
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Tom Ward (941-350-2463)
8977 MIDNIGHT PASS RD #222, SARASOTA, FL 34242
$589,900160 Days on yellowkey MLS ID: A4676582
58 Days Off yellowkey (back on 4/17/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1093 Built: 1974 Tax: $5,552 (2025)Community: Sunrise Cove Sec 3Condo
Taxes:$5,552
Remarks: Under contract-accepting backup offers. Luxury Waterfront Living Spectacular Views, Resort-Style Amenities Wake to breathtaking sunrises over Little Sarasota Bay and the Intracoastal Waterway. This fully remodeled and furnished 2-bedroom, 2-bath condo offers 1,093 square feet of refined coastal living where the views are the true centerpiece. The Residence Thoughtfully renovated in 2024, this residence blends the modern finishes with timeless coastal elegance. The open living and dining areas are bathed in natural light and perfectly positioned to capture sweeping water views, creating an inviting space for both everyday living and entertaining. Features include: 2 Bedrooms, 2 Bathrooms 1,093 Square Feet Panoramic Bay & Intracoastal Views Luxury Vinyl Flooring (2024) New Stainless-Steel Appliances (2024) New Hot Water Heater (2024) New A/C System (2025) Quartz Countertops Offered Fully Furnished with Upscale Furnishings & Accessories Move-In Ready Resort-Style Waterfront Community Enjoy an amenity-rich lifestyle designed for relaxation, wellness, and recreation: Tennis & Pickleball Courts Two Heated Pools-Including an Olympic-Size Pool with Lap Lanes Clubhouse with Pool Table and Ping Pong Fitness Center with Weight & Exercise Equipment Boat Docks Available for Lease Waterfront Setting with Direct Intracoastal Access An Unmatched Coastal Location Turtle Beach directly across the road Shuttle stop providing easy access to Siesta Beach and Siesta Village World-class beaches, boating, dining, and shopping just minutes away The Lifestyle This home is all about the views- sparkling water, passing boats, and unforgettable sunrises enjoyed from the comfort of your living space. Whether as a primary residence, seasonal retreat, or investment property, this condo delivers a luxury waterfront lifestyle with effortless ease.
Listing is courtesy of: PETER D DONAHUE LICENSED REAL ESTATE BROKER (239-206-0740)
Listing Agent: Peter Donahue (239-206-0740)
1365 HARBOR DR, SARASOTA, FL 34239
$5,495,000194 Days on yellowkey MLS ID: A4672827
REDUCED by $490,000 (8.2%) on 04/11/2026
Bed: 4 Bath: 4.5 Gar: 6 Liv Area Sq Ft: 4978 Built: 2018 Tax: $34,839 (2025)Community: Harbor AcresSpa: YesSingle Family
Taxes:$34,839
Remarks: A striking triumph of modern architecture and engineering, this three-story contemporary estate in Harbor Acres—Sarasota’s most coveted neighborhood—stands as a bold statement of design, innovation, and uncompromising luxury. Designed by renowned architect Mark Sultana of DSDG Associates, the residence is a masterwork where precision and artistry converge. From the moment of entry, soaring ceilings, expansive walls of glass, and a dramatic Italian floating staircase set the tone. Natural light fills the interiors, enhancing a layout designed for both impact and livability. The main level is anchored by an open-concept great room and a chef’s kitchen of exceptional caliber. A full suite of Miele appliances—including induction cooktop, built-in espresso maker, warming drawers, dual microwaves, and a full-height wine tower—is paired with Dekton countertops and custom Westwood cabinetry. A concealed butler’s pantry with Sub-Zero refrigeration enhances functionality. Living and dining areas flow seamlessly to a covered terrace with a summer kitchen and thermally modified wood ceiling overlooking the private grounds. The north wing is dedicated to a dual-owner’s suite—two private retreats connected by a spa bath with floating vanities, dual rain showers, soaking tub, heated towel racks, and custom Italian closets. One suite is currently configured as a refined office. The second living level offers a library/media room that can convert to a two-room guest suite, an additional bedroom suite, and two full baths for comfort and privacy. Outdoors, a resort-style setting unfolds with a dramatic 50-foot heated pool and spa, covered lounge areas, and lush bamboo for privacy. A separate one-bedroom guest house with full bath, coffee bar, and mini refrigerator provides independent accommodations. The rooftop terrace captures sweeping panoramic views of Sarasota Bay, the Ringling Bridge, Longboat Key, Siesta Key, and the downtown skyline—an exceptional setting for sunset gatherings. Additional features include Crestron-controlled lighting, shades, and audio, integrated speakers, five Luma security cameras with remote access, and two climate-controlled garages for up to six vehicles with epoxy floors, storage, and a gym opening to the pool terrace. A rare architectural statement offering elevated design, privacy, and location just minutes from downtown Sarasota and the Bayfront.
Listing Agent: Kim Ogilvie (941-951-6660)
1313 SIESTA BAYSIDE DR #1313D, SARASOTA, FL 34242
$639,000144 Days on yellowkey MLS ID: A4678960
REDUCED by $30,000 (4.5%) on 04/17/2026
Bed: 1 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 959 Built: 1988 Tax: $6,865 (2025)Community: Gulf & Bay Club BaysideCondo
Taxes:$6,865
Remarks: Welcome to 1313 Siesta Bayside Drive in Gulf & Bay Club Bayside, a beautifully updated 2-bedroom, 1.5-bath condo offered turnkey furnished and ideally suited as a personal beach retreat or high-performing investment property with weekly rental flexibility and consistent future bookings already in place. This light-filled residence features tasteful coastal updates and a serene pond waterview, complemented by a private single-car garage, driveway parking, and additional guest parking conveniently located across the street. Enjoy deeded beach access to world-famous Siesta Beach, renowned for its bright white quartz sand and crystal-blue Gulf waters, just a short walk away, while the Siesta Key Village shops and restaurants are an easy drive, bike, or golf cart ride. Gulf & Bay Club Bayside is a gated, resort-style community offering two heated pools, tennis and pickleball courts, walking paths, a fishing pier, fitness center, clubhouse, BBQ and picnic areas, and lush tropical landscaping, delivering the perfect blend of relaxed island living and strong income potential in one of Siesta Key?s most desirable communities.
Listing Agent: Shane Lewis (941-685-3252)
1714 SOUTH DR, SARASOTA, FL 34239
$2,245,00085 Days on yellowkey MLS ID: A4686448
Bed: 4 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 3105 Built: 1950 Tax: $11,204 (2025)Community: Cherokee ParkSpa: NoSingle Family
Taxes:$11,204
Remarks: One or more photo(s) has been virtually staged. Tucked beneath a canopy of mature trees in one of Sarasota’s most coveted neighborhoods, 1714 South Drive presents a rare opportunity to secure a prime homesite in Cherokee Park, West of the Trail and moments from the very best of Sarasota living. Set on a beautifully established lot with lush, mature landscaping, a paver driveway, and a combination of garage and carport parking, the property offers an immediate sense of privacy and presence. Inside, the home unfolds with a surprisingly expansive footprint and a floor plan that captures natural light throughout. A welcoming entry with a leaded stained-glass door opens to multiple living spaces, including a living room with a wood-burning fireplace, custom built-ins, and distinctive Saltillo tile flooring, alongside a light-filled family room wrapped in windows with views of the pool and direct access to the lanai. The dining room, positioned with a bay window overlooking the pool, connects seamlessly to the kitchen, which features granite countertops, glass-front cabinetry, a center island with cooktop, and a breakfast nook with access to a private side deck. The layout offers flexibility with multiple bedroom and office options, including a front bedroom or office with a wall of windows and an in-wall safe, and a private guest suite with its own bath showcasing vintage turquoise tile and retro detailing. A secondary guest bedroom includes built-in workspaces and shelving, ideal for dual office use or creative space. The primary suite is tucked privately toward the rear of the home, offering direct access to the lanai, abundant natural light, and a spacious bath with dual vanities, soaking tub, walk-in shower, and skylight above. Additional spaces include a bonus room off the garage with bedroom conversion potential, a pool bath, and a separate flex space off the lanai with wood-paneled walls and its own mini-split system, ideal for a studio, gym, or additional lounge. Outdoors, the home continues to deliver with an oversized, caged pool and covered lounging areas, surrounded by mature landscaping, stone walkways, and a fully fenced yard. An existing outdoor kitchen structure and multiple access points from the home create a true indoor-outdoor flow that aligns perfectly with Sarasota’s year-round lifestyle. What truly elevates this property is its location. Just moments from the shops and restaurants of Southside Village or downtown Sarasota’s waterfront, cultural venues, and marina. It is close to Sarasota Bay and just a short drive to Siesta Key’s north bridge. This is a setting that defines convenience and coastal luxury. Cherokee Park remains one of the most desirable addresses in Sarasota, and 1714 South Drive offers the rare combination of location, lot, and layout, an exceptional opportunity in the heart of Sarasota.
4078 GROVELAND AVE, SARASOTA, FL 34231
$345,000227 Days on yellowkey MLS ID: A4669478
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1240 Built: 1981 Tax: $2,704 (2024)Community: Grove ParkSingle Family
Taxes:$2,704
Remarks: In a city where home prices often feel out of reach, this well-maintained three-bedroom, one-bath residence offers something increasingly rare: a real opportunity to plant roots in Sarasota without sacrificing location or potential. Set on a quiet, non-HOA neighborhood just minutes from the beach, downtown, shopping, and restaurants, this home proves that owning in Sarasota does not mean choosing between charm, location, and affordability. Inside, you will find an open layout with tile and laminate flooring, natural light throughout, and a warm, welcoming feel ready to be personalized. The kitchen has been thoughtfully updated with granite countertops and refreshed cabinetry that seamlessly blends function and simplicity, while unifying the living and dining areas. A cozy brick fireplace, featuring an above-mantel TV mount, anchors the living room, making it perfect for both quiet evenings with a book and hosting game day with friends. The primary bedroom features two closets and a dual-access ensuite bath that connects to the hallway leading to the home's two additional bedrooms. Step outside to a fully fenced backyard with a spacious deck, fire pit, and a large permitted shed that offers flexibility for storage or creative use, along with ample room for a home addition or pool, if desired. While it is not the biggest or flashiest house in town, it is real, it is ready, and it can be yours to shape. Whether you are a first-time buyer looking to stay in Sarasota on a budget, a seasonal visitor in need of a winter retreat, or someone who values authenticity, this is a home where you can begin to build not just equity, but a meaningful life. A 1% RATE BUY-DOWN IS AVAILABLE TO QUALIFIED BUYERS WHO WORK WITH THE SELLER'S PREFERRED LENDER.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Domanic Calamese (941-914-0038)
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