Location: Sarasota, 34231
Do Not Show Listings
5911 OLIVE AVE, SARASOTA, FL 34231
$375,00091 Days on yellowkey MLS ID: A4688660
REDUCED by $10,000 (2.6%) on 04/27/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1324 Built: 1957 Tax: $3,537 (2025)Community: Golden AcresSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,537
Elementary School: Gulf Gate Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: One or more photo(s) has been virtually staged. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**Located in a quiet residential neighborhood just 3.7 miles from Siesta Key, this well maintained Florida ranch offers a combination that is getting harder to find. Close proximity to the beach, no HOA, and the added peace of mind of being in flood zone X. This three bedroom, two bath home on an oversized lot features a split floor plan with a primary suite that includes a walk in closet and en suite bath. The kitchen has been updated with granite countertops and opens into the main living space, creating a comfortable and functional layout for everyday living. Recent updates make this home truly move in ready, including brand new luxury vinyl plank flooring and fresh interior paint in 2026. Additional improvements include roof in 2015, HVAC in 2017, electrical panel in 2015, repipe in 2015, and water heater in 2016. The Florida room offers flexible bonus space that can be used as a home office, additional living area, or seasonal room. Out back, the fully fenced yard provides plenty of space to spread out, whether for pets, play, or storing a boat, trailer, or other toys. With no HOA, you have the flexibility to actually use your property. Whether you are looking for a full time residence, a seasonal place near the beach, or an investment opportunity, this location delivers. Just minutes to Siesta Key, shopping, and dining, with a level of flexibility that is hard to find this close to the water. Schedule your private showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Ashley Wallace (941-302-2586)
2551 WILKINSON RD, SARASOTA, FL 34231
$389,90026 Days on yellowkey MLS ID: A4696791
REDUCED by $10,000 (2.5%) on 06/26/2026
Bed: 3 Bath: 0.0 Liv Area Sq Ft: 1469 Built: 1955 Tax: $3,559 (2025)Community: Forest HillsApartment
Taxes:$3,559
Elementary School: Phillippi Shores Elementary
Remarks: Virtually Staged. A Piece of Sarasota History Meets Modern Opportunity: The "Siesta Key Style" Duplex with TWO separate electrical panels! Own a landmark piece of Sarasota history. Nestled on an expansive, wooded double lot at the western end of Wilkinson Road, this "Siesta Key style" bungalow offers a rare blend of timeless character and modern updates. Surrounded by a lush, quarter-acre canopy of mature bamboo, majestic oaks, and tropical palms, this property is a private sanctuary just minutes from the best of the Gulf Coast. Two units, endless potential and fully remodeled between 2023 and 2024, this versatile duplex is an ideal setup for savvy investors, multi-generational families, or those looking to "house-hack". Unit 1: A spacious 2-bedroom, 2-bathroom layout. Unit 2: A charming 1-bedroom, 1-bathroom retreat. Modern Upgrades & Peace of Mind: Every major system has been addressed so you can enjoy "turn-key" living or immediate rental income. Roof: New commercial-grade TPO membrane roof (2022) with a 30-year life. Climate: Brand new, energy-efficient mini-split AC systems in both units. Infrastructure: New plumbing throughout and separate electrical panels for each side. Interior: A fresh mix of new and restored flooring, newer appliances in unit 1, and stylish finishes. Exterior: Extra storage in the outdoor shed and plenty of room to roam & garden on the oversized lot. Location is Everything!!! Whether you’re heading to the beach, to work or to the city, you are perfectly positioned: 5 Minutes to the North Siesta Key Bridge. 12 Minutes to the vibrant culture and dining in Downtown Sarasota. 11 Minutes to the freeway for easy commuting. Don't miss this rare chance to own a functional, fully updated landmark in one of Sarasota’s most convenient locations. Some photos are visually staged. Schedule your private tour today!
Listing is courtesy of: BOUDRIE REAL ESTATE GROUP INC (941-730-5674)
Listing Agent: Rebekah Boudrie (941-730-5674)
$389,90053 Days on yellowkey MLS ID: A4691540
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1469 Built: 1955 Tax: $3,559 (2025)Community: Forest HillsSingle Family
Remarks: A Piece of Sarasota History Meets Modern Opportunity: The "Siesta Key Style" Duplex with TWO separate electrical panels! Own a landmark piece of Sarasota history. Nestled on an expansive, wooded double lot at the western end of Wilkinson Road, this "Siesta Key style" bungalow offers a rare blend of timeless character and modern updates. Surrounded by a lush, quarter-acre canopy of mature bamboo, majestic oaks, and tropical palms, this property is a private sanctuary just minutes from the best of the Gulf Coast. Two units, endless potential and fully remodeled between 2023 and 2024, this versatile duplex is an ideal setup for savvy investors, multi-generational families, or those looking to "house-hack". Unit 1: A spacious 2-bedroom, 2-bathroom layout. Unit 2: A charming 1-bedroom, 1-bathroom retreat. Modern Upgrades & Peace of Mind: Every major system has been addressed so you can enjoy "turn-key" living or immediate rental income. Roof: New commercial-grade TPO membrane roof (2022) with a 30-year life. Climate: Brand new, energy-efficient mini-split AC systems in both units. Infrastructure: New plumbing throughout and separate electrical panels for each side. Interior: A fresh mix of new and restored flooring, newer appliances in unit 1, and stylish finishes. Exterior: Extra storage in the outdoor shed and plenty of room to roam & garden on the oversized lot. Location is Everything!!! Whether you’re heading to the beach, to work or to the city, you are perfectly positioned: 5 Minutes to the North Siesta Key Bridge. 12 Minutes to the vibrant culture and dining in Downtown Sarasota. 11 Minutes to the freeway for easy commuting. Don't miss this rare chance to own a functional, fully updated landmark in one of Sarasota’s most convenient locations. Some photos are visually staged. Schedule your private tour today!
1858 MARBETH ST, SARASOTA, FL 34231
$412,50046 Days on yellowkey MLS ID: A4694568
1 Days Off yellowkey (back on 6/26/2026)
REDUCED by $12,500 (2.9%) on 06/05/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1199 Built: 1986 Tax: $3,647 (2025)Community: VamoHalf Duplex
Taxes:$3,647
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. DUPLEX...Live in one side and rent the other side. One Building with two units with 2 bedrooms and 1 bath each. Addresses are 1856 and 1858 Marbeth Street. Both units have their own washer/dryer. The building is on NEW septic tank AND County water with one meter...(the landlord pays the low water bill without a sewer bill.). New electric panel and there is a owner's shed in the back. One unit was just repainted inside. The back yard is fenced. There is a newer septic tank and lift station. Each unit's electric is metered separately and tenant pays electric bill. Tenants just moved out. One tenant was paying $1,700/Month and the other tenant was paying $1795/Month. $412,500
Listing is courtesy of: VUE REALTY, LLC (941-269-8400)
Listing Agent: Scotty Ledford (941-400-7360)
1856 MARBETH ST, SARASOTA, FL 34231
$412,50047 Days on yellowkey MLS ID: A4694543
Bed: 8 Bath: 0.0 Liv Area Sq Ft: 1199 Built: 1986 Tax: $3,647 (2025)Community: North Vamo Sub 2Spa: NoApartment
Remarks: Under contract-accepting backup offers. DUPLEX...One Building with two units with 2 bedrooms and 1 bath each. Addresses are 1856 and 1858 Marbeth Street. Both units have their own washer/dryer. The building is on NEW septic tank AND County water with one meter...(the landlord pays the low water bill without a sewer bill.). New electric panel and there is a owner's shed in the back. One unit was just repainted inside. Located in the most desired "X" flood zone AND 3 blocks from the new multi use Sarasota Square mall REUSE/REBUILD Project bringing a lot of jobs/job opportunities just walking distance away! The back yard is fenced. There is a newer septic tank and lift station. Each unit's electric is metered separately and tenant pays electric bill. Tenants just moved out. One tenant was paying $1,700/Month and the other tenant was paying $1795/Month. $412,500
1648 STARLING DR #202, SARASOTA, FL 34231
$320,000159 Days on yellowkey MLS ID: A4680410
REDUCED by $5,000 (1.5%) on 06/24/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1975 Built: 1987 Tax: $4,982 (2025)Community: Landings South VCondo
Taxes:$4,982
Middle School: Booker Middle
Remarks: One or more photo(s) has been virtually staged. LET'S MAKE A DEAL! Take advantage of a $5,000 incentive at closing, yours to use as you choose toward a decorating or flooring allowance, HOA fees, or closing costs. Positioned as one of the best buys in The Landings, with arguably the best location and amenities the community offers, this beautifully maintained second-floor coach home delivers standout value. A brand new roof, gutters, AC, exterior paint, resurfaced roads, and a brand new community pool set the stage in The Landings, one of Sarasota's most established guard-gated communities. Tucked at the end of a private cul-de-sac just one block from the pool and community amenities, the setting offers privacy and convenience in equal measure, with the big-ticket items already handled. A private entry framed by distinctive tile steps opens to a light-filled interior where soaring vaulted ceilings give the space an immediate sense of openness. Wide-plank wood flooring runs through the main living areas, connecting each room with an easy flow while keeping the dining, living, and kitchen spaces nicely defined. Just off the living area, an enclosed lanai lined with expansive sliding glass doors looks out over peaceful treetops, a quiet spot equally suited to morning coffee or winding down in the evening. At the heart of the home, the kitchen balances function and warmth with white cabinetry, granite countertops, custom tile backsplash detailing, and a sunlit eat-in area. A breakfast bar opens to the living and dining rooms for effortless entertaining, while a built-in dry bar adds character, extra storage, and a natural spot to serve guests. The primary suite carries the same vaulted ceilings and includes a flexible alcove that works beautifully as a sitting area or home office, along with a dedicated dressing space, built-in storage, and an oversized walk-in closet. Its en-suite bath offers a walk-in shower with bench seating, generous counter space, and timeless finishes. Two additional bedrooms and a guest bath round out the layout, leaving room for visitors, hobbies, or a work-from-home setup. Life here is genuinely maintenance-free. The HOA covers the roof, windows, sliders, screens, exterior paint, landscaping, pest control, cable and Xfinity service, and insurance from the drywall out. The home sits approximately 21 feet above sea level and is not in a flood zone, an increasingly meaningful detail on the Gulf Coast. Residents of The Landings enjoy the Racquet Club with tennis and pickleball, resort-style and lap pools, a fitness center, clubhouse, and an active social calendar, plus a scenic nature trail leading to Roberts Bay, where a kayak launch and fishing dock offer direct access to the water. A private garage with attic storage, a paver driveway, and convenient guest parking complete this move-in-ready residence, close to the beaches, dining, and culture that define Gulf Coast life. Come experience the comfort and ease of The Landings for yourself. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Toni Zarghami (941-248-2147)
3165 REGATTA CIR, SARASOTA, FL 34231
$459,000130 Days on yellowkey MLS ID: A4683961
REDUCED by $5,900 (1.3%) on 06/05/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1193 Built: 1964Monthly Fee: $6 Tax: $3,638 (2025)Community: Gulf GateSingle Family
Taxes:$3,638
Remarks: Under contract-accepting backup offers. Completely remodeled with all work permitted and completed to the highest standards, this move-in ready Gulf Gate home lives large and showcases exceptional quality, thoughtful design, and true craftsmanship. Live where others vacation — perfectly positioned just 2.4 miles from the nearest Siesta Key beach access, placing world-renowned white sand beaches and breathtaking Gulf sunsets just minutes from your doorstep! The designer-curated kitchen features solid wood white shaker cabinetry, premium quartz countertops, a custom tile backsplash, and new stainless-steel appliances. Just off the kitchen, a spacious dining area is anchored by a beautifully crafted custom solid wood banquette with an integrated bookcase, bench seating, and built-in storage — a rare and functional design feature. Both full bathrooms have been beautifully renovated with new vanities, updated countertops, and custom tiled showers. Additional interior upgrades include new luxury vinyl plank flooring, fresh interior and exterior paint, new doors and trim, and updated lighting & fixtures. Indoor laundry adds everyday convenience. Major system improvements provide peace of mind, including new PVC underground sewer drain lines, new water lines, a new water heater, updated electrical panel, HVAC (2020), and a *BRAND NEW ROOF* (2026)! All windows are equipped with hurricane shutters. Designed for seamless indoor/outdoor living, multiple sliding glass doors open to a spacious screened and covered back porch featuring upgraded Trex decking — the perfect space for morning coffee or relaxed evenings under the twinkle lights. The backyard is truly special, highlighted by a custom PAVER FIRE PIT with built-in bench seating. Enjoy fresh landscaping, a new front paver walkway, and a large fenced backyard. Covered carport parking includes an outdoor storage closet, plus an additional shell parking space which provides plenty of parking. Centrally located on a quiet circle in prime Gulf Gate, this home offers easy access to world-famous Siesta Key Beach and is within walking or biking distance to an array of local restaurants and shopping in Gulf Gate. Publix, Trader Joe’s and Costco are all just minutes away, and Gulf Gate Elementary School is right around the corner. Turnkey furnishing option is also available which could make for an easy second home. Bright, cheerful, and beautifully finished — this home is truly move-in ready! Buyer’s agent to verify all MLS information including room sizes, utilities and HOA if applicable.
Listing is courtesy of: CARMEL PROPERTIES (941-416-6300)
Listing Agent: Jonah Wright (941-932-1661)
2763 WOODGATE LN #211, SARASOTA, FL 34231
$180,00012 Days on yellowkey MLS ID: A4698193
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 874 Built: 1979Monthly Fee: $595 Tax: $2,156 (2025)Community: Pinewood Village IiCondo
Taxes:$2,156
Remarks: Delightful 2-bedroom, 2-bath condo in an unbeatable Sarasota location! Beautifully maintained and move-in ready, this spacious home is just 15 minutes from the world-famous Siesta Key Beach and the vibrant dining, shopping, and cultural attractions of Downtown Sarasota. The recently renovated kitchen offers a fresh, modern feel, while the generous floor plan provides comfort, convenience, and easy Florida living. Additional updates include a new A/C (2023) for added peace of mind. The current tenant is scheduled to move out in September 2026, making this an excellent opportunity for a first-time homebuyer looking to move right in, while also offering investors immediate rental income until then. To provide even greater peace of mind, the seller is including a one-year home warranty, paid at closing. Whether you're searching for your first home, a seasonal retreat, or a smart investment, this Sarasota gem is one you won't want to miss.
Listing is courtesy of: PALM PARADISE REALTY GROUP (239-955-7256)
Listing Agent: Maria Domenech (978-204-3219)
5929 MURDOCK AVE, SARASOTA, FL 34231
$449,97788 Days on yellowkey MLS ID: A4687404
0 Days Off yellowkey (back on 5/14/2026)
REDUCED by $14,973 (3.2%) on 05/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1711 Built: 1957 Tax: $1,644 (2025)Community: Golden Acres 1St AddSingle Family
Taxes:$1,644
Remarks: Under contract-accepting backup offers. Virtually Staged. From the moment you arrive, you will immediately notice the combination of an oversized driveway, garage, and covered carport. With room for multiple vehicles, guests, a boat, or weekend toys, this is the type of flexibility you hope for. That's not a stone roof either.... It's an ALL NEW Decra metal roof which gives the home a clean, updated look while adding long-term value and protection. Located at 5929 Murdock Ave, this Sarasota home has been fully renovated with the updates that matter most. Inside, you’ll find new vinyl flooring throughout, fresh paint, updated bathrooms, and hurricane-impact sliders that bring in natural light while adding peace of mind during storm season. The major systems have already been addressed as well, including all new electrical and plumbing that has been professionally scoped, giving the next owner confidence in what they’re walking into. Every update was made with everyday living in mind — creating a home that feels fresh, functional, and ready to enjoy from day one. More than just cosmetic improvements, this is a home where the work has already been done, allowing its next owner to simply move in and make it their own in Sarasota. Updates: 2019 Permit - Mechanical change out - HVAC System - new heat pump - rear unit, 2021 All new LVP flooring throughout the main house, 2021 Installed fence around back yard, 2022 New dishwasher, 2023 Permit - Re-Roof - Decra stone coated metal roof Installed by RoofTech Roofing & Waterproofing, Inc, 2023 New garbage disposal, 2023 Septic tank pumped with full inspection & maintenance, 2023 Installed all new water valves throughout the house, Bathrooms, kitchen & laundry room, 2024 Permit - Rewiring the entire house, new electrical panel, outlets, switches & all new fixtures. Also installed a whole house surge protector at the panel, 2024 Installed new tankless water heater, 2024 Installed new door between the garage and kitchen to meet FBC (was glass door before), 2024 New upgraded stainless steel kitchen sink, 2024-25 Re-screened rear porch, 2025 Full master bathroom remodel, 2026 Full hall bathroom remodel, 2026 Interior Paint, 2026 Exterior paint, 2026 Installed new impact glass sliding doors in living room & master bedroom.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Vincent Diorides (941-720-5717)
7503 STARFISH DR, SARASOTA, FL 34231
$499,90068 Days on yellowkey MLS ID: A4691968
REDUCED by $15,100 (2.9%) on 06/25/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1383 Built: 1957Monthly Fee: $21 Tax: $3,608 (2025)Community: Coral CoveSingle Family
Taxes:$3,608
Remarks: Welcome to 7503 Starfish Drive in desirable Sarasota, Florida—an exceptional opportunity to own a slice of paradise just minutes from world-renowned Siesta Key Beach. Nestled in the sought-after Coral Cove subdivision, this charming residence offers the perfect blend of comfort, convenience, and coastal living. This well-maintained home features a spacious and functional layout with abundant natural light throughout. The living areas flow seamlessly, creating an inviting atmosphere ideal for both everyday living and entertaining. The kitchen offers ample cabinetry and workspace, ready for your personal touch or future upgrades. Step outside to enjoy your private outdoor space—perfect for relaxing, hosting gatherings, or adding a pool to create your own backyard oasis. The property provides plenty of room to customize and make it your own. One of Coral Cove’s standout features is its private community boat ramp, offering residents convenient access to the Intracoastal Waterway for a minimal annual fee—an exceptional perk for boating enthusiasts. Ideally located, you’re just a short drive to Siesta Key’s sugar-white sands, top-rated dining, shopping, and entertainment. With easy access to major roadways and downtown Sarasota, this home is perfectly positioned for both full-time living and seasonal enjoyment. Whether you’re looking for a primary residence, vacation home, or investment property, this is an opportunity you don’t want to miss.
Listing is courtesy of: REALTY EXECUTIVES GALLERY (941-376-8769)
Listing Agent: Troy Jenkins (941-376-8769)
2492 WATERVIEW CT, SARASOTA, FL 34231
$995,00074 Days on yellowkey MLS ID: A4691223
1 Days Off yellowkey (back on 6/15/2026)
REDUCED by $100,000 (9.1%) on 05/28/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2017 Built: 1955Monthly Fee: $38 Tax: $4,717 (2025)Community: Riverview ManorSpa: NoSingle Family
Taxes:$4,717
High School: Sarasota High
Middle School: Sarasota Middle
Remarks: Looking for a home with boating access in your backyard, yet still mainland and close to everything you need? Welcome to 2492 Waterview Ct in Sarasota! This home was substantially renovated in early 2024 and offers 3 bedrooms, 2 bathrooms, 2 car garage, pool, and dock with 4,500 lb boat lift on Phillippi Creek. You'll have peace of mind with a 2023 roof, all impact windows and doors, and knowing this home had NO WATER INTRUSION from any recent storms. Entering the home from the double front entry door, you'll be impressed with premium grade white oak engineered hardwood flooring throughout the home, high ceilings, new baseboards, trim, interior doors, and tons of natural light shining in. A spacious living room and dining room combination offers separation between your primary suite and spare bedrooms. The kitchen has quartz countertops, tons of cabinetry, a large pantry, and an eat in area perfect for a breakfast table or banquet. Enjoy subtle water views from your primary bedroom featuring a completely renovated ensuite bath with marble countertops, dual sinks, jet tub, frameless glass shower, water closet, and walk-in closet with custom built in shelving. On the other side of the home, you'll find a hallway with storage closet, a full bathroom with dual sinks and a shower/tub combination, along with two spare bedrooms - each housing dual closets with custom shelving. A laundry room with sink and cabinetry is located off the kitchen near the garage entry. Both areas of the main living space offer sliding glass doors leading out to a spacious patio and open-air pool that was completed in 2020. The fully fenced yard is perfect for pets, kids, and privacy. Walk through your backyard down to the creek and find a private boat dock with lift ready for you to enjoy countless days out on the beautiful waters surrounding Sarasota with just a quick boat ride to get to the main channel. You'll enjoy summer nights with the lively atmosphere and vibes of the Phillippi Creek boating community with your neighbors out and about on the water. The two-car garage has plenty of cabinetry for storage, along with a separate room plumbed for a full bath or whatever you want to make of it to suit your needs. Enjoy the privacy of this 1/3 acre lot knowing you'll never have a neighbor to the left side due to a large grassy retention pond area. Riverview Manor has very low HOA dues coming in at only $450 per year. You are minutes from the Landings shopping plaza and everything 41 has to offer, as well as less than 10 minutes to the North or South Bridge to Siesta Key, and less than 15 minutes to Downtown Sarasota. With water access, a boat lift and dock, renovated home, pool, and prime location, there is not much more you could be looking for! Schedule your showing today.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Victoria Beckham (941-544-6734)
2144 OAK TER, SARASOTA, FL 34231
$455,00078 Days on yellowkey MLS ID: C7525020
REDUCED by $10,000 (2.2%) on 06/10/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1769 Built: 1979 Tax: $4,601 (2025)Community: Harbor OaksSpa: NoSingle Family
Taxes:$4,601
Remarks: Single story home in move-in ready condition with an abundance of natural light throughout (and a new roof!). The bedrooms are generously sized, and bathrooms are well maintained. The home also offers an oversized garage with additional storage potential. NO HOA FEES! Easy to show!
Listing is courtesy of: SOVEREIGN REAL ESTATE GROUP (305-662-1502)
Listing Agent: William Figueroa (305-662-1502)
2852 NASSAU ST, SARASOTA, FL 34231
$344,90087 Days on yellowkey MLS ID: A4689690
REDUCED by $7,600 (2.2%) on 06/25/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1344 Built: 1996 Tax: $4,033 (2025)Community: Virginia Heights SubSingle Family
Taxes:$4,033
Remarks: Virtually Staged. PRICE IMPROVEMENT!! This beautifully updated two-story home offers 3 bedrooms, 2 bathrooms, and a spacious open loft across 1,344 square feet of living space. The primary bedroom is conveniently located on the first floor. The renovated kitchen features shaker-style cabinets, stainless steel appliances, and sleek quartz countertops, while both bathrooms have been tastefully updated. Luxury vinyl plank flooring runs throughout the first floor of the home and carpet on the 2nd, adding both style and durability. Enjoy the convenience of a one-car garage and relax on the private deck overlooking a peaceful preserve and running brook. Nestled on a quiet dead-end street, this home is ideally located less than 4 miles from Siesta Key Beach and close to shopping, dining, schools, hospitals, and downtown amenities.
Listing is courtesy of: ALLEGIANT REAL ESTATE GROUP (941-685-3958)
Listing Agent: Lori Campbell (941-685-3958)
3049 GYPSY ST, SARASOTA, FL 34231
$399,00060 Days on yellowkey MLS ID: A4693010
REDUCED by $26,000 (6.1%) on 06/25/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 980 Built: 1981 Tax: $3,612 (2025)Community: Madison ParkSingle Family
Taxes:$3,612
Elementary School: Wilkinson Elementary
Remarks: Welcome to 3049 Gypsy Street, a beautifully updated, coastal-inspired retreat being offered turnkey furnished (minus personal property), making it the perfect opportunity for a first-time homebuyer, snowbird or savvy investor looking for immediate income potential. Previously operated as a highly rated Airbnb, this charming Sarasota home is move-in ready and set up to continue generating rental income from day one. Inside, discover a light and bright interior featuring luxury vinyl plank flooring throughout, a spacious living and dining area and a stunning remodeled kitchen complete with white cabinetry, stainless steel appliances, a farmhouse sink, a beautiful white 3D backsplash and all appliances included. The split-bedroom layout offers two spacious bedrooms and two completely renovated baths. The primary suite features a brand-new bath with a large walk-in shower, while the guest bedroom comfortably accommodates multiple guests with a full and twin bed. Outdoor living shines with a charming covered coastal-style lanai complete with a ceiling fan, shell paver patio area, fully fenced backyard, new landscaping and plenty of room for a future pool. There is also separate RV/boat parking on the side of the home for added flexibility or plenty of room for a pool. Additional highlights include a new roof (2022), a sewer connection completed in 2021, a one-car garage with a washer, dryer, utility sink and storage. Turnkey furnished opportunity: this was previously a successful Airbnb with a rental history. Ideally near all Sarasota has to offer, including world-famous beaches, dining, shopping, arts and entertainment, this adorable coastal getaway offers a blend of lifestyle and investment opportunity.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-907-9541)
Listing Agent: Jaci Krawtschenko (941-284-3789)
2717 RIVERBLUFF PL #V49, SARASOTA, FL 34231
$270,000138 Days on yellowkey MLS ID: A4681632
0 Days Off yellowkey (back on 6/25/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1480 Built: 1971Monthly Fee: $725 Tax: $2,787 (2025)Community: Strathmore Riverside IVilla
Taxes:$2,787
Remarks: Under contract-accepting backup offers. Mrs. Clean Lives Here! Absolutely Charming 2 bed/2bath end-unit Villa! Stunning kitchen that gently flows into dining room area Thw Dining room area opens into large living room with another large family room area creating LOTS of living space A bonus room with the ability to make this your own game room, office space, or just your own oasis! Crown molding in living and dining room with gorgeous wood flooring. Separate storage and laundry room for your convenience Plenty of Guest parking and carport near your front door. This lovely community has a Clubhouse, community pool, fitness, activity calendars, and a Marina ( annual fee is approximatley $1344- annually ). Close to fabulous restaurnants and shops, Detweilers Famers Market and the South bridge to world famous Siesta Key! Freshly Painted within this last year! Active Community with clubhouse facility, community Pool and marina (CHECK)! This is a stunning villa with an exceptional location, just minutes to Siesta Key, shopping and fine dining! If you are looking to live the Sarasota lifestyle come checkjk on this breathtaking villa TODAY!!
Listing is courtesy of: SHOWTIME REALTY (941-822-0890)
Listing Agent: Marcia Morse (941-374-0442)
1703 STARLING DR #1703, SARASOTA, FL 34231
$675,000263 Days on yellowkey MLS ID: A4668895
REDUCED by $24,000 (3.4%) on 06/25/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2172 Built: 1993 Tax: $4,481 (2024)Community: Landings, Villas At Eagles PointCondo
Taxes:$4,481
Tax Year: 2024
Remarks: Welcome to carefree living in The Landings. This beautifully remodeled townhome makes carefree living an absolute dream! Not an inch has gone untouched, showcasing modern luxury finishes. Whether you're looking to winter in Sarasota or enjoy all that The Landings Racquet Club has to offer all year long, you are sure to relish coming home. The first-floor primary bedroom is very spacious, with an equally comfortable en suite and custom walk-in closet. The large back lanai features perfect privacy. There is a loft or family room upstairs, just outside the additional two bedrooms; perfect for an office, playroom, or sitting area. The neighborhood offers a 24-hr manned security gate, a world-class tennis and pickleball facility, pool, fitness center, and clubhouse. You'll never need to leave! But when you choose to venture out, popular restaurants and shopping are just outside the gates!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Tracy Leclair (941-209-0549)
4147 AUGUSTINE AVE, SARASOTA, FL 34231
$395,00014 Days on yellowkey MLS ID: A4697916
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1500 Built: 1958 Tax: $4,984 (2025)Community: Floral Park HomesteadsSingle Family
Taxes:$4,984
Remarks: Under contract-accepting backup offers. Situated on a premium quarter-acre lot with no HOA or CDD fees, this 3 bedroom 2 bath concrete block home perfectly blends modern design with everyday functionality. The sleek, chef-inspired kitchen serves as the anchor for an expansive open floor plan, making entertaining effortless.Designed for elegant living, the layout features a private home office, surround sound wiring, a cozy fireplace, and an exceptionally large Primary Suite with a spa-style bath. Practical upgrades include a tankless water heater, new roof, AC with warranty and a spacious inside laundry room. Abundant storage throughout. Outside, a massive lanai offers the perfect backdrop for Florida relaxation, and a newer fenced in yard for privacy. Plenty of room for parking a boat or RV. Located on a quiet side street close to downtown Sarasota, hospital,shopping and Siesta Key Beach. This turnkey-ready home is perfect as a primary residence, second home, or as a lucrative investment.
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Laurine Gauthier (941-586-3929)
5430 MATTHEW CT, SARASOTA, FL 34231
$499,90048 Days on yellowkey MLS ID: A4692322
REDUCED by $12,000 (2.3%) on 06/25/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1629 Built: 1995Monthly Fee: $33 Tax: $3,760 (2025)Community: Forest OaksSingle Family
Taxes:$3,760
Remarks: 5430 Matthew Court is nestled at the end of a peaceful cul-de-sac in Sarasota’s highly desirable Forest Oaks community. This inviting 3-bedroom, 2-bath residence instantly feels like the Florida home you are seeking. It features two spacious primary suites, making it ideal for multi-generational living or hosting guests. Step inside to discover a thoughtfully designed floor plan. The home includes QUARTZ COUNTERTOPS, PORCELAIN TILE FLOORING, UPDATED CABNETRY, 2023 APPLIANCES/ WASHER/DRYER, TANKLESS HOT WATER HEATER, HURRICANE RESISTANT FRONT WINDOW, ELECTRIC/CRANK METAL SHUTTERS, RE-PIPED, TREX DECKING, 2024 MASTER SHOWER FLOOR RE-TILED and 2023 INTERIOR AND EXTERIOR PAINT. Seller currently using electric appliances but natural gas is available. Whether you are seeking a full-time residence, seasonal getaway, or income-producing investment, this versatile property is ready to fit your needs. Location is everything and this home delivers. It is just minutes from the powdery white sands of world-famous Siesta Key Beach. Families will appreciate being situated within a top-rated school district. Riverview High School is a walk or bike ride away. Walk to Red Bug Slough, a scenic 72-acre preserve. The preserve offers shaded walking trails, picnic areas, and birding opportunities. In addition, you’ll enjoy effortless access to premier shopping, dining, and entertainment, when based at this residence. 5430 Matthew Court combines a prime central location with both privacy and convenience. This home captures the very best of the Florida lifestyle.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Kadie Nolan (941-404-6192)
6688 SCHOONER BAY CIR #6688, SARASOTA, FL 34231
$755,00050 Days on yellowkey MLS ID: A4693436
1 Days Off yellowkey (back on 6/25/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1812 Built: 1988 Tax: $3,716 (2025)Community: Schooner BayCondo
Taxes:$3,716
Remarks: Under contract-accepting backup offers. Tucked within the quiet gated boating community of Schooner Bay, this beautifully remodeled 3 bedroom, 2 bath, 2 car garage waterfront condo blends relaxed Florida living with effortless boating convenience just minutes from Siesta Key’s world-famous white sand beaches. With over 1,800 square feet of thoughtfully designed living space and a 23-foot boat dock and boat lift just outside your door, this residence is perfectly suited for those looking to fully embrace the coastal boating way of life. A semi-private side entrance welcomes you inside, where a distinctive front-to-back view immediately draws your eye through the expansive sliding glass doors to the peaceful saltwater canal beyond. Light wood-look vinyl flooring, high sloped ceilings, oversized front windows, and an open-concept layout create a bright and airy atmosphere filled with natural light. The crisp white kitchen features bar-top seating, counter-to-ceiling tile backsplash, recessed lighting, stainless steel appliances, and seamless flow into the dining and living areas, ideal for both relaxed daily living and gathering with guests. Just beyond, the enclosed sunroom provides a relaxing extension of the living space with picturesque canal views and a tranquil setting to enjoy morning coffee or unwind at the end of the day. The spacious primary suite offers private access to the sunroom through sliding glass doors, peaceful water views, a walk-in closet, and an en suite bath complete with a dual sink vanity, separate shower, and private toilet room. Two generously sized guest bedrooms share a second full bath, offering comfort and flexibility for family or visitors. Residents of Schooner Bay enjoy access to a clubhouse and heated community pool, along with an unbeatable location just minutes from Siesta Key Beach which is consistently ranked among the best beaches in the world for its soft white sand and turquoise waters. From here, you’re also close to a variety of local dining, casual waterfront restaurants, boutique shopping, and vibrant entertainment, all just a short walk or bike ride away. Crisp, comfortable, and inviting, this condo delivers the best of easy living– with boating from your private dock, beach days on Siesta Key, and peaceful canal views right at home. A rare opportunity to enjoy it all in one place, this is a home you truly need to see today!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Karie Backman (941-404-8389)
2609 WOODGATE LN #K4, SARASOTA, FL 34231
$149,90083 Days on yellowkey MLS ID: N6143915
REDUCED by $10,000 (6.3%) on 06/25/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1100 Built: 1982Monthly Fee: $588 Tax: $2,358 (2025)Community: Pinewood Village IxCondo
Taxes:$2,358
Remarks: You're five miles from one of the best beaches in America. You just didn't know you could afford to live this close. Ground floor, pool-facing, fully furnished 2BR/2BA in Pinewood Village. Walk out your lanai and you're at the pool. Walk out the front door and Siesta Key Beach, St. Armands Circle, Marina Jack, and downtown Sarasota are minutes away. The best-priced unit in the community — and better than anything else available right now. Ground floor instead of stairs. Tile throughout instead of carpet. Fully furnished and move-in ready the day you close. The only comparable unit in this section spent 385 days on the market and just went pending. This one won't last that long. Flood Zone X. No flood insurance required — a real financial advantage in today's Sarasota market. Outside your door, Sarasota delivers everything. Sarasota Memorial Hospital three miles away. Phillippi Estate Park around the corner. The Van Wezel, the Asolo, the Ringling, the Opera — ten minutes from your front door. The restaurants, the boutiques of St. Armands, the farmers markets, the sailing — all of it yours. Pinewood Village itself overdelivers at this price. Heated pool, fitness center, sauna, shuffleboard, full clubhouse with kitchen. HOA covers cable, water, sewer, trash, pest control, exterior maintenance and building insurance. Phillippi Shores Elementary, Brookside Middle, Riverview High. Association approval required. Sold As-Is. Seller motivated.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Jeffery K. Twigg, Pa (941-412-6505)
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