Location: Sarasota
Do Not Show Listings
9489 SWAYING BRANCH RD, SARASOTA, FL 34241
$2,695,000109 Days on yellowkey MLS ID: A4675577
0 Days Off yellowkey (back on 3/31/2026)
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 4537 Built: 2015Monthly Fee: $342 Tax: $1,701 (2024)Community: Forest At The Hi Hat RanchSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,701
Elementary School: Lakeview Elementary
High School: Riverview High
Tax Year: 2024
Middle School: Sarasota Middle
Remarks: Under contract-accepting backup offers. Welcome to 9489 Swaying Branch Road, a beautifully designed residence located within The Forest at Hi Hat Ranch, an exclusive 270-acre gated community comprised of just 54 estate-sized homesites. This intimate Sarasota enclave is defined by its no-repeat architectural rule, ensuring every home is custom built and truly one of a kind. Surrounded by mature landscaping and preserved natural beauty, the community offers a rare balance of luxury, privacy, and tranquility. This thoughtfully crafted 4-bedroom, 4-bathroom single-family home spans over 4,500 square feet of living space and is ideally positioned on a premium homesite that is over 3 Acres with peaceful lake views from the rear, along with conservation and street views that enhance both privacy and scenery. The open, flexible floor plan is designed for effortless entertaining and everyday comfort, featuring expansive living areas, soaring ceilings, and abundant natural light throughout. At the heart of the home, the kitchen is designed for both function and gathering, showcasing quality finishes, generous cabinetry, and seamless flow into the main living spaces. Well-appointed bedrooms and bathrooms provide comfort and privacy for family and guests, while additional bonus spaces provide versatility for a home office, media room, or flex living area. Outdoor living is equally impressive, with a screened pool and spa, covered lanai, and tranquil views that create an ideal setting for year-round enjoyment. Notable upgrades include impact-rated windows for hurricane protection, a whole-home generator for uninterrupted peace of mind, a 4-car garage, irrigation system, and a private setting immersed in nature. Residents of The Forest at Hi Hat Ranch enjoy a secure, gated lifestyle just minutes from Sarasota’s top-rated schools, shopping, dining, and cultural attractions—while still feeling worlds away from it all. This is a rare opportunity to own a spacious, custom home in one of Sarasota’s most exclusive low-density communities.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Brian Wood (941-928-8408)
1533 OAK WAY, SARASOTA, FL 34232
$879,00095 Days on yellowkey MLS ID: A4678901
3 Days Off yellowkey (back on 3/31/2026)
Bed: 5 Bath: 3.5 Liv Area Sq Ft: 3231 Built: 1988Monthly Fee: $172 Tax: $8,039 (2025)Community: Lakes Estates 3 Of SarasotaSingle Family
Taxes:$8,039
Elementary School: Brentwood Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: McIntosh Middle
Remarks: Under contract-accepting backup offers. Set on nearly half an acre in the heart of The Lakes Estates, a sought after community with mature trees and winding roads, 1533 Oak Way offers a rare combination of space, serenity and central Sarasota convenience. Surrounded by mature trees and positioned on higher ground, this five-bedroom residence feels private and elevated, literally and figuratively. A welcoming front porch sets the tone, inviting you into a thoughtfully laid-out home with five bedrooms, three full baths and an additional half bath on the first floor, ideal for everyday living and hosting. Natural light fills the interior, while the home’s screened back porch provides a peaceful place to unwind and enjoy the lush, tree-filled surroundings. The expansive lot offers ample room to add a pool, creating opportunity to design your private outdoor oasis, an increasingly rare feature in such a centrally located neighborhood. Peace of mind comes standard with a roof replaced just two years ago, allowing you to focus on enjoying the home rather than future maintenance. The Lakes Estates is beloved for its resort-style amenities, including two community pools, a clubhouse, recreation center, playground and tennis courts, offering something for every age and lifestyle. Just minutes from downtown Sarasota, shopping, dining, beaches and top schools, this location puts all things Sarasota within easy reach. Opportunities like this, large lots, established neighborhoods and central proximity, are increasingly hard to find. Don’t miss your chance to own a standout home in one of Sarasota’s sought-after communities.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Katy Mcbrayer (941-400-2406)
4628 ASHBERRY DR, SARASOTA, FL 34234
$275,00057 Days on yellowkey MLS ID: A4683659
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 954 Built: 1985 Tax: $1,079 (2025)Community: Spring OaksSingle Family
Taxes:$1,079
Elementary School: Emma E. Booker Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Welcome to this charming 1985 concrete block ranch home offering nearly 1,000 square feet of living space — all on one level. Featuring 2 bedrooms and 2 bathrooms, the layout is comfortable and functional, providing a wonderful foundation to update at your own pace. This home has been lovingly maintained by its original owner and was originally the model home for the development. Major improvements are already complete, including impact windows and doors throughout, a brand-new roof (2025), new hot water heater (2025), and A/C replaced in 2021 — offering peace of mind on the big-ticket items. Tucked away on a quiet street, yet just minutes to SRQ Airport, Downtown Sarasota, shopping, dining, beaches, and major thoroughfares, the location offers both privacy and convenience. While cosmetic updates would enhance the space, the home offers solid block construction, pride of ownership, and long-term potential in a central Sarasota location. Being sold As-Is. A rare opportunity to personalize a well-cared-for home with exceptional fundamentals already in place. Please be aware that the home does smell like cigarette smoke.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Evan Weber (941-287-9700)
161 S POLK DR, SARASOTA, FL 34236
$5,999,000159 Days on yellowkey MLS ID: A4672276
REDUCED by $251,000 (4.0%) on 03/31/2026
Bed: 5 Bath: 5.0 Liv Area Sq Ft: 4617 Built: 2013 Tax: $88,251 (2024)Community: Lido BeachSingle Family
Taxes:$88,251
Elementary School: Southside Elementary
Remarks: In a world where more is usually never enough……. 161 S. Polk Drive is JUST ENOUGH and MORE OF EVERYTHING YOUR DREAMS ARE MADE OF! Positioned waterfront between St. Armands Circle and Lido Beach, you can start your day walking just one block to put your toes in the sand and soak up the morning sun and then head straight to your favorite lunch spot on the circle. Upon returning home, take up lounging in the split-level, salt water pool and relax to the sounds of the water as it crests the infinity edge OR you can choose one of the many decks, from rooftop on down, canal to Gulf, to savor the sun, the breeze, the views and the peacefulness all around you. Once evening arrives, hop on the boat for a pleasant ride to your waterfront dining of choice or enjoy a glass of wine as you unwind with soothing music, the gentle movement of the water and savor the setting sun. This privately gated, coastal contemporary home encompasses over 4,600 square feet of interior living space with an open plan from living to dining to kitchen and on to the outdoor patio with a full wall of pocketing sliders. The acacia wood floor will be the first to grab your eye, but you will then be drawn to the unlimited other features of this home. From the many windows offering abundant natural light, to the built-ins, wet bars, oversized kitchen island, 3 en-suite bedrooms all with private balconies (includes first and 2nd floor owner suites), elevator, outdoors showers, sauna, ‘hidden’ oversized laundry room with 2 sets of washers and dryers, oversized boat dock with 2 lifts……. Shall I go on?? The well thought out configuration of this home rationalizes JUST ENOUGH of comfortably elegant entertaining mixed with intimate peace and privacy. Recent improvements include A/C handlers and compressors, tankless water heater and pump, flat tile roof decking, refinished exterior wood railings, pool pumps and actuators, in-ground drainage system, refreshed landscaping, exterior pressure washing, recent elevator service completed
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Cindy Schatzle (941-587-7556)
2375 BAHIA VISTA ST, SARASOTA, FL 34239
$512,000246 Days on yellowkey MLS ID: A4662778
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1092 Built: 2022 Tax: $5,587 (2024)Community: Avon Heights 2Single Family
Taxes:$5,587
Elementary School: Alta Vista Elementary
Middle School: Brookside Middle
Remarks: Elevate your lifestyle in this unique island-style home in the heart of Sarasota! An exceptional opportunity to experience the best of Florida living and an effortless move-in with all turnkey furnishings included, allowing you to settle in immediately. The interior is bright, optimized, and beautifully finished with luxury vinyl floors, shaker style cabinets, smooth finish doors, and smart TVs throughout, creating a modern and inviting atmosphere. The spacious living room and alcove with an antique bar cart and desk are adjacent to the dining area and a fully equipped kitchen, featuring elegant stone countertops and "smart" Samsung stainless steel appliances—ideal for entertaining guests or enjoying family meals. For your convenience, the interior laundry area includes a Samsung washer and dryer. This delightful home, built in 2022 to current building codes, ensures peace of mind with optimal construction features including impact windows, durable metal roof, and elevated stilt-on-concrete-piling construction with ample under-building carport style parking for two cars. With three bedrooms and two full baths, it comfortably sleeps eight, making this home perfect for families or groups. Located in a coveted area between vibrant downtown Sarasota and gorgeous Gulf Coast beaches, you can easily walk to Arlington Park and Aquatic Complex, head to Lido Key Beach or world-famous Siesta Key Beach with its quartz crystal sand, or simply relax in the serene, tree-lined backyard. This home is currently used as a part-time vacation home and for weekly vacation rentals. It's ideal as a full-time residence, a convenient part-time vacation home, or for continued weekly rentals, offering flexible ownership options. You will also love the close proximity to Sarasota's vibrant arts and culture scene, diverse dining venues, Sunday Farmers Market, the stunning Sarasota Bayfront and marina, and abundant recreational activities.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Dennis Kotaska, Llc (941-815-6772)
1903 24TH ST, SARASOTA, FL 34234
$279,000186 Days on yellowkey MLS ID: A4668435
2 Days Off yellowkey (back on 3/31/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1684 Built: 1964 Tax: $2,479 (2024)Community: Epsteins Add To NewtownSingle Family
Taxes:$2,479
Remarks: Under contract-accepting backup offers. Experience Refined Sarasota Living in the heart of Sarasota—where timeless charm meets contemporary comfort. This beautifully appointed residence embodies the essence of the Old Florida lifestyle, offering an ideal blend of location and convenience. Perfectly situated just moments from Downtown Sarasota, this home provides effortless access to the city’s premier beaches, cultural landmarks, and vibrant dining scene. Property Highlights include Light-Filled Interiors, expansive living spaces designed to capture Sarasota’s signature sunshine. Elegant finishes with tasteful Florida-inspired details are throughout the home. A generous yard ideal for entertaining, gardening, or creating your private retreat under the palm trees. Enjoy the proximity to Sarasota’s most coveted destinations. Bask in coastal beauty at Lido Key beach or the powder-white sandy beach of world-renowned Siesta Key—each less than 20 minutes away. Immerse yourself in Sarasota’s cultural scene with The Ringling Museum, Van Wezel Performing Arts Hall, and a collection of premier galleries just minutes from your door. Explore Main Street’s boutique shopping, fine dining, and vibrant nightlife in one of Florida’s most desirable urban enclaves. Paddle through the mangroves at South Lido Nature Park, hike Myakka River State Park’s scenic trails, or unwind at picturesque Bayfront Park. Whether you seek a sophisticated full-time residence, a SMART investment opportunity, or an elegant seasonal escape, 1903 24th St delivers exceptional value and endless potential in one of Florida’s most prestigious coastal cities.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: David Halligan (941-815-6690)
4801 SARASOTA AVE, SARASOTA, FL 34234
$560,000392 Days on yellowkey MLS ID: A4646529
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1492 Built: 1959 Tax: $6,465 (2023)Community: Sapphire HeightsSingle Family
Taxes:$6,465
Elementary School: Bay Haven Sch of Basics Plus Elementary
High School: None
Tax Year: 2023
Middle School: None
Remarks: AS SEEN IN THE WEEK MAGAZINE! Live the best that the Florida lifestyle has to offer with this remodeled mid-century modern pool home located in the desirable Indian Beach Sapphire Shores neighborhood. This midcentury gem has been completely updated including the kitchen and baths, roof, plumbing, electric, and the pool. The 2-ply polyglass roof was replaced in 2020, the AC system in 2021, and the minisplit AC system in 2020. All of the original cast iron plumbing has been replaced with PVC pipes and fittings. The copper water pipes have been replaced with modern PEX pipes and fittings. The electrical panel was updated in 2021 and the heated pool has been rebuilt. All you need to do is move-in and begin enjoying the sunshine in your fully fenced backyard. Adding to the backyard oasis vibes is an oversized screened patio which has enough space to create an outdoor living room and dining area. Inside the home is clean and bright with renovated kitchen and bathrooms and clever built-in storage solutions. The kitchen features a wall length built-in pantry as well as stainless appliances and ample cabinet storage. The large and flexible living space features two walls of windows and a beautiful living room built-in with storage space, display space, and integrated seating.The primary suite features an en-suite renovated bathroom as well as a private entrance to the backyard. While located outside the flood plain you still have easy access to multiple neighborhood parks along Sarasota Bay; they are a fantastic place to watch the sunset, fish, or launch your paddleboards and kayaks into Sarasota Bay. The low-cost and optional Indian Beach Sapphire Shores neighborhood association offers a neighborhood newsletter, picnics, and additional social activities. Driving, walking, or biking along the neighborhood's shaded streets and sidewalks you'll be treated to a tour of Sarasota architecture from the 1920s through today. Within the neighborhood you will also find cultural amenities including the Ringling Museum which features frequent community event programming and the Asolo Theatre which houses Asolo Rep as well as the Sarasota Ballet. Both Downtown Sarasota and Sarasota Bradenton Airport are a 5 minute drive from the home. Shopping and dining on St Armands Circle and the crystal quartz sand of Lido Beach is just a 10 minute drive.
Listing Agent: Amanda Gilliland (941-320-1132)
2343 EUGENE ST, SARASOTA, FL 34231
$449,90039 Days on yellowkey MLS ID: A4686269
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1352 Built: 1984 Tax: $3,729 (2025)Community: Pinehurst Park Rep OfSingle Family
Taxes:$3,729
Elementary School: Gulf Gate Elementary
Remarks: Rare opportunity just minutes from Siesta Beach. This three-bedroom home offers the perfect Florida retreat—whether you’re seeking a primary residence, seasonal getaway, or income-producing investment with a proven track record. Ideally located in South Sarasota, just two miles from the world-famous white sand beaches of Siesta Key, this home blends relaxed coastal living with comfortable modern updates. Inside, an inviting open floor plan fills with natural light and creates an effortless flow between the living, dining and kitchen areas—perfect for everyday living and entertaining. The updated kitchen overlooks the main living space and features solid surface countertops, a peninsula with breakfast seating, and a striking subway tile backsplash that extends to the ceiling. Stylish luxury vinyl flooring runs throughout the home, while sliding glass doors open to the backyard to create a seamless indoor-outdoor lifestyle. Enjoy sunny days on the spacious outdoor deck or relax on the separate patio—ideal for grilling, gathering with friends, or unwinding after a day at the beach. Thoughtful touches throughout the home include beautifully finished bathrooms and a convenient laundry room - perfect for sandy beach towels. This property has been well maintained with recent exterior paint and offers a long driveway with room for an RV. With no HOA or deed restrictions, you’ll enjoy flexibility and freedom rarely found this close to Siesta Key. Located near highly rated schools, shopping, dining, and Sarasota’s renowned arts and cultural scene, this charming home offers an easygoing coastal lifestyle just moments from the Gulf. Furniture Negotiable.
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: Sarah Lowry (941-400-9026)
3878 ROYAL HAMMOCK BLVD, SARASOTA, FL 34240
$849,90088 Days on yellowkey MLS ID: D6145789
REDUCED by $30,000 (3.4%) on 03/31/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2497 Built: 2003Monthly Fee: $138 Tax: $7,519 (2025)Community: HammocksSingle Family
Taxes:$7,519
Elementary School: None
Remarks: What a gorgeous home featuring.. 4 bedrooms/3 bathrooms/3 car garage and pool with spa located in The Hammocks (A Gated Community). As you walk though this double entry door a freshly painted home awaits you and you are greeted with views of the Living Room/Dining Room overlooking the newly rennovated pool area with Storm shade for extra protection. If you love to cook then this kitchen is for you! This kitchen was totally rennovated with all new appliances, center island, beautiful wood cabinets, gorgeous quartz counter tops, new fixtures, large pantry and Luxury vinyl tile. The kitchen has a nice eating area with large window overlooking the pool area and open to the Family room that has sliders out to the pool area. On one side of the home, you will find 3 nice size guest bedrooms with 2 guest bathrooms one of which leads out to pool & lanai area and one that has been totally rennovated. On the opposite side of the home you will find the luxurious primary suite that features sliders out to pool & lanai area with an absolutely stunning En Suite that was completely redone with dual sinks, large soaking tub and beautiful walk in shower. The outside of this home is just as lovely as it features a large corner lot with luscious landscaping and Fresh paint. Also adding to this beautiful home is a newly installed rainsoft water treatment for the whole house. The location of this home is perfect as it is only 10 miles to the gulf if you're seeking a beach day! This home truly is one of a kind that has been loved and meticulously maintained. You won't be disappointed. Please see 3D tour and the list of total updates that is attached to this listing.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-429-3506)
Listing Agent: Debbie Jones (941-228-2849)
2022 29TH ST, SARASOTA, FL 34234
$250,000114 Days on yellowkey MLS ID: A4676565
0 Days Off yellowkey (back on 2/4/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1510 Built: 2000 Tax: $1,403 (2025)Community: Newtown TerraceSingle Family
Taxes:$1,403
Remarks: Under contract-accepting backup offers. INVESTOR ALERT!!! Major Price Adjustment!!! 3BR/2BA single-family home built in 2000 on a .28-acre lot, located near downtown Sarasota with convenient access to major roadways. Well-suited for fix-and-flip or long-term buy-and-hold strategies. Detached structure/ADU on site is a tear-down, with utilities already in place.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Jacob Wessels (941-999-1179)
611 TREMONT ST, SARASOTA, FL 34242
$3,399,00099 Days on yellowkey MLS ID: A4678455
Bed: 4 Bath: 5.0 Liv Area Sq Ft: 4194 Built: 2005 Tax: $21,457 (2025)Community: Siestas BaysideSingle Family
Taxes:$21,457
Elementary School: Phillippi Shores Elementary
Remarks: A spectacular offering on one of Siesta Key’s most coveted streets, this stunning canal-front residence on Tremont Street represents a truly special opportunity to own a home that seamlessly blends boating, timeless island charm, and refined coastal living. Tucked beneath mature trees in a quiet, established enclave known for its old Siesta character, the property offers private canal frontage with a lift and a short, easy boat ride to the Intracoastal Waterway, all just minutes from Siesta Village and the world-renowned white sands of Siesta Beach. Homes of this caliber and setting are seldom available and must be experienced in person to be fully appreciated. Offering 4,194 square feet under air, the thoughtfully designed floor plan is both impressive and highly livable, ideal for full time residents and seasonal owners alike. Soaring ceilings, abundant natural light, and quality craftsmanship define the interior. The main floor primary suite is complemented by additional bedrooms on the main level, providing the ease of one level living, while the second floor offers a spacious guest suite and bonus room with peaceful views of the pool and canal. Exceptional indoor-outdoor living is at the heart of the home. Multiple pocketing sliding glass doors open wide to an expansive covered and fully screened lanai, creating a seamless connection between interior and exterior spaces. The outdoor living area is generous in scale and designed for entertaining, featuring a heated pool and spa, summer kitchen, gas fireplace, and multiple areas for dining and relaxation. The large screened layout allows you to comfortably enjoy outdoor living year round, regardless of the weather. Lush tropical landscaping enhances privacy and creates a tranquil island setting, while boating enthusiasts will appreciate the private lift and convenient access to open water. Impact-rated windows and doors, a generator, and a three-car garage provide peace of mind and everyday practicality. 611 Tremont Street combines location, boating, and lifestyle in a way few homes can. If you have been waiting for an exceptional Siesta Key property in one of the island’s most desirable neighborhoods, this is one you should see in person before it sells.
Listing Agent: Mike Warm, Llc (941-525-2740)
2244 PALM TER, SARASOTA, FL 34231
$595,00043 Days on yellowkey MLS ID: A4684326
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1680 Built: 1961 Tax: $5,135 (2025)Community: RidgewoodSingle Family
Taxes:$5,135
Remarks: Under contract-accepting backup offers. DOUBLE LOT. SEE ATTACHED LETTER FROM COUNTY STATING 2 HOMES CAN BE BUILT ON PROPERTY. HOME IS RENTED UNTIL JUNE OF 2026. Will consider sale if interested but lease will need to be honored. View Matterport Virtual Tour LINK 2 . Nestled in a secure, family-oriented neighborhood, the home's charm begins at the curb. The thoughtfully landscaped surroundings and inviting exterior set the stage for the warmth and comfort found within. This 3-bedroom, 2-bath home underwent a thoughtful and complete renovation in 2020, ensuring every detail contributes to a welcoming atmosphere. Everything from the new roof, windows, doors, flooring, cabinetry, pool and landscaping was freshly upgraded. The heart of the home, the kitchen, is a chef's delight with high-end appliances, granite countertops, glass tile backsplash, soft-closing cabinetry and remote controlled custom lighting. The primary bedroom offers a retreat of tranquility with a walk-in closet and a spa-like bathroom featuring an oversized tub, shower, and double sinks. 3rd Bedroom with seating area, 20 x 17 with its own door to patio / pool. An open concept layout allows for seamless transitions between spaces while French door in the family room draws your eyes outside and connects you with nature. As you step into the backyard, you're greeted by a true Floridian retreat. An in ground heated pool, jacuzzi, and ample space for play and relaxation create an ideal outdoor haven. The smart irrigation system, butterfly, herb garden, and fruit trees contribute to the vibrant landscape.. Both front and back yards feature automated lights, creating a magical ambiance as they illuminate at dusk. Convenience is key with this home's proximity to downtown Sarasota and 10 minutes to #1 Siesta Key beach. Great dining near-by including; Geckos, Tripletail, Walt's Fish Market, Brine, Ruth's Chris and much more. 3rd Bedroom with seating area, 20 x 17 with its own door to patio / pool. All Measurements approximate. Buyer should review all room sizes. PROPERTY CURRENTLY LEASED UNTIL 6/1/2026 AT $3,800/MO. + UTILITIES, OCCUPANCY NEGOTIABLE.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Tracy Srodes (813-267-1312)
5110 ADMIRAL PL, SARASOTA, FL 34231
$559,90037 Days on yellowkey MLS ID: A4686260
1 Days Off yellowkey (back on 3/31/2026)
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1816 Built: 1971 Tax: $3,544 (2025)Community: Phillippi ShoresSingle Family
Taxes:$3,544
Remarks: Under contract-accepting backup offers. Waterfront living on Phillippi Creek with direct access to Sarasota Bay and the Gulf. This lovely 2-story home offers 3 bedrooms, 3 bathrooms, and 1,816 square feet of living space in a prime Sarasota location with no HOA. The kitchen was renovated in 2017 and features quartz countertops, a pantry, and a sleek touchless faucet, while new tile flooring enhances the lower level. Upstairs, both bedrooms include walk-in closets, and the living area opens to an expansive wraparound deck—an ideal space to unwind, enjoy the coastal breeze, and take in the peaceful water views. Whether you're starting your morning with coffee or winding down at sunset, the setting is truly special. Major updates include impact windows installed in 2022, a new HVAC system and water heater in 2026, and a 15-year roof sealant added in 2025. Foam insulation in the lower level adds comfort and efficiency, and a new utility sink was added to the laundry room in 2026 for everyday convenience. Step outside and enjoy a front-row seat to nature, where manatees are often seen, creating a serene and memorable backdrop. The Phillippi Creek fixed bridge is located less than 0.75 miles from the home—Enjoy kayaking or from your backyard with access to Sarasota Bay and the Intracoastal Waterway—ideal for flat boats and smaller vessels. . Perfectly positioned, this home is just minutes from The Landings Shopping Center, Southside Village, downtown Sarasota, and the world-famous Siesta Key Beach. Located within an A+ rated school district, this property offers not only an exceptional lifestyle, but lasting value. 3D tour of the home by clicking on the virtual tour link #2.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Tessa Robbins, Pa (941-374-1345)
2314 N OSPREY AVE, SARASOTA, FL 34234
$255,00025 Days on yellowkey MLS ID: TB8491942
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 760 Built: 1959 Tax: $2,171 (2025)Community: NewtownSingle Family
Taxes:$2,171
Elementary School: Wilkinson Elementary
Remarks: Location! Location! The seller is highly motivated and encourages you to bring all offers. This updated 3-bedroom, 1-bath concrete home features several key improvements, including roof, HVAC system, LED lighting, flooring, and fresh paint throughout. The kitchen and bathroom were previously updated. Additionally, the property includes a fully fenced yard. The home is conveniently located near downtown Main Street, the Ringling Museum, and the Sarasota Bradenton Airport.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Ivey Shelley (941-544-1129)
5439 CARTAGENA DR, SARASOTA, FL 34233
$699,00025 Days on yellowkey MLS ID: A4687951
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 2420 Built: 2014Monthly Fee: $194 Tax: $4,204 (2025)Community: Ashton PointeSingle Family
Taxes:$4,204
Elementary School: Ashton Elementary
Remarks: Located in the gated community of Ashton Pointe, this upgraded pool home at 5439 Cartagena Drive, Sarasota, FL 34233 offers the ideal blend of modern design, outdoor living, and prime Sarasota location, just 7.6 miles to Siesta Key Beach and minutes to Downtown Sarasota, I-75, Publix, top-rated schools, dining, and shopping. Built in 2014, this 4-bedroom, 2 full + 1 half bathroom Sarasota pool home features an open-concept floor plan designed for both everyday living and entertaining. The fully updated kitchen features quartz countertops, stainless steel appliances, wood cabinetry, under-cabinet lighting, and a large island, all flowing seamlessly into the main living and dining areas. Upstairs, all bedrooms are privately situated along with a versatile loft/bonus room ideal for a home office, media room, or gym. The spacious primary suite includes a custom walk-in closet, dual vanities, soaking tub, and glass-enclosed shower, while the upstairs laundry room adds everyday convenience. The standout feature is the resort-style outdoor living space, a true backyard oasis. The screened lanai includes a custom pool with a large heated spa, app-controlled system, outdoor bar with commercial-grade ice bin sink, remote-controlled awning, multiple covered seating areas, and two outdoor TVs, perfect for entertaining or relaxing in true Florida lifestyle fashion. Additional upgrades include crown molding, updated lighting and fans, Low-E thermal windows, tile roof, in-wall pest system, security cameras, and exterior outlets for lighting. Low HOA fees include lawn care, irrigation, and landscaping, offering a low-maintenance, maintenance-free lifestyle in one of Sarasota’s most desirable gated communities. This Sarasota Florida home for sale is ideally located near Siesta Key, Downtown Sarasota, Ashton Pointe, and major conveniences, making it a rare opportunity to own a gated community pool home with spa, modern upgrades, and true indoor-outdoor living. This is one of the best opportunities for a Sarasota pool home near Siesta Key with upgraded features, outdoor entertaining space, and prime location.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Noah Ward (715-531-8021)
420 ARCHIBALD AVE, SARASOTA, FL 34243
$399,77726 Days on yellowkey MLS ID: A4687979
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1013 Built: 1975 Tax: $789 (2025)Community: Tuxedo ParkSingle Family
Taxes:$789
Elementary School: Florine J. Abel Elementary
High School: Bayshore High
Middle School: Electa Arcotte Lee Magnet
Remarks: Nicely updated 2 bedroom, 2 bathroom block home in a great central location between downtown Sarasota and downtown Bradenton. Located outside of a flood zone and just minutes from Sarasota Airport, University Parkway, shopping, dining, and about 15–20 minutes to the beach. This 1975 home has been refreshed inside and out. Major updates include a brand new roof (2025), impact windows, new HVAC system, new garage door with opener, and a new paver driveway (all 2026). Inside, you’ll find tile flooring throughout, upgraded 5 1/4” baseboards, light fixtures, fresh interior and exterior paint, and more. The kitchen features quartz countertops, shaker-style cabinets, and a full stainless steel appliance package. Both bathrooms have been updated with a clean, modern look. The layout is simple, functional, and easy to maintain. The back lanai adds a great outdoor space for relaxing or entertaining. This would make a solid primary residence, rental, or an easy Florida vacation home with low maintenance and many big-ticket items already taken care of. Home is vacant, staged, and easy to show/see. Schedule a showing today!
Listing is courtesy of: RELAX PROPERTY GROUP, LLC (941-923-7200)
Listing Agent: Dane Peterson (239-357-5692)
1040 SYLVAN DR, SARASOTA, FL 34234
$1,495,00025 Days on yellowkey MLS ID: A4687776
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1949 Built: 1980 Tax: $15,027 (2025)Community: Sylvan ShoresSingle Family
Taxes:$15,027
Remarks: An exceptional opportunity awaits to create your dream waterfront retreat in one of Sarasota’s most desirable locations. This unique property offers the rare chance to either complete the existing structure to your exact specifications or design and build a custom home tailored to your vision. Set on a private, serene lot surrounded by lush greenery, the property provides a peaceful, tucked-away feel while still being remarkably close to everything Sarasota has to offer. Enjoy excellent boating water with direct access to Sarasota Bay and the Gulf, making it a true paradise for boating and water sport enthusiasts. The property is already equipped with a dock and boat lift, so you can start enjoying the waterfront lifestyle right away. Located on a quiet, tree-lined street, this homesite combines tranquility with convenience. You’ll be just minutes from Bayfront Park, downtown Sarasota’s vibrant shops and restaurants, the Ringling Museum, Sarasota-Bradenton International Airport, and the University Town Center. Whether you envision a modern coastal masterpiece or a timeless waterfront estate, this is a rare chance to bring your vision to life in an unbeatable location with outstanding boating access and exceptional privacy.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Jennifer Linehan (941-266-7555)
3217 OAK GROVE DR, SARASOTA, FL 34243
$810,000309 Days on yellowkey MLS ID: A4656185
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2537 Built: 1996Monthly Fee: $8 Tax: $8,993 (2024)Community: Oak Grove ParkSingle Family
Taxes:$8,993
Remarks: One-of-a-Kind custom retreat on OVER an Acre in Prime Location in the highly sought after Oak Grove Subdivision! With no deed restrictions and an optional $100/year HOA you will enjoy the serenity of feeling like you are in a private zen retreat but minutes from all the amenities. Past the long paver driveway you will discover this unique 3 bedroom, 2.5 bathroom home featuring a 2-car garage plus a detached workshop with a screened porch and equipped with A/C - perfect for hobbies, storage, or extra space. The interior features a split plan with an open kitchen/ family room, versatile living room/dining area, vaulted ceilings, double panel solid wood doors and charming arches. The kitchen showcases a large breakfast bar, beautiful solid surface counters and a built in workstation. The spacious primary bedroom offers an en-suite bathroom with walk-in closets including built in storage and a garden tub! From morning coffee to evening happy hour, the screened patio is the perfect spot to unwind and relax with friends and family. The sparkling heated pool area overlooks beautifully manicured gardens, creating a tranquil backdrop for peaceful outdoor living. The home’s Spanish-inspired architecture adds charm and character, making it truly one of a kind. The owners have taken impeccable care and pride in keeping the original charm while adding personal touches. This private oasis offers a serene escape and is a rare find in a convenient and highly desirable area located less than 4 miles from SRQ airport, 5 miles from University Town Center and 10 miles from the beautiful gulf beaches. This home offers a Sarasota address with Manatee County taxes— don’t miss your chance to own this distinctive unique property!
Listing Agent: Nicole Hearn (941-524-6133)
1758 35TH ST, SARASOTA, FL 34234
$101,200345 Days on yellowkey MLS ID: A4652687
0 Days Off yellowkey (back on 3/4/2026)
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 979 Built: 1959 Tax: $2,710 (2024)Community: Amaryllis ParkSingle Family
Taxes:$2,710
Remarks: 3 bd 1 bath bungalow investment property only. Has recently had a fire and extensive damage to roof and AC. Near downtown Sarasota. Large back yard. One block from Robert Taylor Community Center. 15 minutes from downtown, Beaches, Hospital, shopping and freeway. No Deed Restrictions.
Listing is courtesy of: SPECIALIZED REAL ESTATE LLC (941-966-6836)
Listing Agent: Otto Hajek (941-966-6836)
7893 PEACEFUL PAR DR, SARASOTA, FL 34241
$560,00094 Days on yellowkey MLS ID: A4678259
1 Days Off yellowkey (back on 3/3/2026)
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2041 Built: 2016Monthly Fee: $220 Tax: $6,773 (2025)Community: Fairways/Bent TreeSingle Family
Taxes:$6,773
Remarks: Under contract-accepting backup offers. Located on a corner lot in The Fairways at Bent Tree, this home offers golf course and lake views in an optional golf community with maintenance-free lawn care. The fenced yard, screened lanai, and heated saltwater pool create the perfect setting for outdoor living. The open floor plan features 3 bedrooms plus a large den, 2.5 baths, and 9’4” ceilings with quality upgrades throughout. The kitchen includes 42” shaker cabinets, granite countertops, slate no-smudge appliances, and a large entertaining island. Tile flooring highlights the living areas, with bamboo flooring in the bedrooms and tray ceilings adding style. FPL Energy Certified with a 15-SEER HVAC, radiant barrier roof sheathing, and double-pane thermal windows. Ideally located less than 2 miles to I-75, 10 minutes to UTC, and approximately 20 minutes to Sarasota’s top beaches. Move-in ready and perfectly positioned for easy, low-maintenance living.
Listing Agent: Mary Michael Martin (941-962-2997)
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