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$2,799,000
4 Beds 3 Baths TB8542235 MLS
Prime investment opportunity directly on prestigious Beach Road in Siesta Key. This fully renovated, raised multi unit property offers strong short term rental income potential in one of Florida's most desirable coastal markets. The side by side duplex features a spacious 2 bedroom, 2 bathroom unit and a 2 bedroom, 1 bathroom unit. Zoned RMF and legally permitted for nightly rentals, making it ideal for vacation rental investors. The current owner is available to continue managing the property for the next owner at only a 10 percent fee, with staff, cleaning crew, and maintenance vendors already in place. The property generated $393,000 in gross income in 2023, $323,000 in 2024 (with two months of downtime due to hurricane impact), and $291,000 in 2025 (still down from hurricane related effects), with 2026 year to date income of $192,000 through July. Recent updates include new AC systems in 2022, updated flooring in 2025, modernized plumbing in 2022, full electrical upgrades in 2022, and private hot tubs installed at each unit in 2022. Additional upside exists with completed engineering drawings to enclose the lower level, adding approximately 2,000 square feet and significant rental income potential. Just steps from the sand and close to Siesta Key Village shops and restaurants, this is a rare chance to own an income producing property in one of the top beach destinations in the country. Property is part of a very successful Airbnb portfolio consisting of three duplexes with cap rates exceeding 10 percent. Please inquire for details.

527 Beach Road, Siesta Key

Listing courtesy of PEOPLE'S TRUST REALTY. 352-688-7022

$2,690,000
6 Beds 4 Baths TB8541886 MLS
Discover an exceptional income producing property in the heart of coveted Siesta Key. This fully renovated multi unit compound features two spacious 3 bedroom, 2 bathroom units, one upstairs and one downstairs, making it ideal for short term rental investors. The current owner is available to continue managing the property for the next owner at only a 10 percent fee, offering a seamless, turnkey transition. The property generated $393,000 in gross income in 2023, $350,000 in 2024 (with two months of downtime due to hurricane impact), and $308,977 in 2025 (still down from hurricane related effects), with 2026 year to date income of $214,000 through July, offering strong and proven cash flow. Recent improvements include new AC (2025), updated flooring (2024 to 2025), modernized plumbing (2024), electrical upgrades (2022), and refreshed hot tubs (2021). What truly sets this property apart is its Commercial General (CG) zoning with a special exemption allowing nightly rentals, a rare and highly valuable designation on Siesta Key that protects the short term rental use. This zoning also unlocks significant redevelopment potential, including the possibility to construct an approximately 85 foot building with ground floor parking, 11 two bedroom units, and a rooftop pool. Property is part of a very successful Airbnb portfolio consisting of three duplexes with cap rates exceeding 10 percent. Please inquire for details.

5228 Calle Menorca, Siesta Key

Listing courtesy of PEOPLE'S TRUST REALTY. 352-688-7022

$479,900
6 Beds 5 Baths O6433142 MLS
Gillespie Park Triplex Investment Opportunity! Located in the highly sought-after Gillespie Park area of Sarasota, this 1,983 SF triplex offers an excellent opportunity to renovate and reposition a multi-unit property in one of Sarasota's desirable in-town locations. The property features three separate units with a total of 6 bedrooms and 3 baths, each having a Kitchen with living/dining combination, providing flexible income-producing potential. Zoned DTE, the property offers a variety of possibilities for an investor or owner looking to create value in a sought-after Sarasota location. Conveniently located near downtown Sarasota, Gillespie Park, restaurants, shopping, entertainment, and the area's beautiful beaches. With its desirable location, three-unit configuration, and redevelopment potential, this property is an excellent opportunity to bring new life to a multi-family asset in an established Sarasota neighborhood. Buyer to verify all zoning, dimensions, uses, and redevelopment possibilities with the appropriate governing authorities. All information recorded in the MLS is intended to be accurate but cannot be guaranteed, buyer advised to verify.

1672 10th Street, North Sarasota

Listing courtesy of ALL FLORIDA PROPERTY GROUP,INC. 321-622-5211

$288,380
3 Beds 2 Baths C7528861 MLS Dr Horton/Cbc#1253536 BLDG.
Under Construction. This beautiful Twin Villa boasts a welcoming open floorplan as you walk in. You will love the beautiful open kitchen with a lot of cabinet storage, a large island, and walk-in pantry, making your home great for cooking and entertaining. All stainless-steel kitchen appliances with oven, microwave, dishwasher, refrigerator, and garbage disposal are included. The Carrington villa has 3 bedrooms and 2 full baths with ceramic tile flooring throughout, tile shower walls, quartz countertops, and impact windows. You'll enjoy the great outdoor space on the large screened in lanai. Lawn care and irrigation is included! Central Parc is a low maintenance, low HOA/CDD, gated community with resort style pool, hot tub, fitness center, clubhouse with full kitchen, tennis, and pickleball courts! Come visit to see if Central Parc is the perfect community for you!

4583 Schubert Trail, North Port

Listing courtesy of DR HORTON REALTY SW FL LLC. 239-338-8986

$288,380
3 Beds 2 Baths C7528810 MLS Dr Horton/ Cbc#1253536 BLDG.
Under Construction. This beautiful Twin Villa boasts a welcoming open floorplan as you walk in. You will love the beautiful open kitchen with a lot of cabinet storage, a large island, and walk-in pantry, making your home great for cooking and entertaining. All stainless steel kitchen appliances with oven, microwave, dishwasher, refrigerator, and garbage disposal are included. The Carrington villa has 3 bedrooms and 2 full baths with ceramic tile flooring throughout, tile shower walls, quartz countertops, and impact windows. You'll enjoy the great outdoor space on the large screened in lanai. Lawn care and irrigation is included! Central Parc is a low maintenance, low HOA/CDD, gated community with resort style pool, hot tub, fitness center, clubhouse with full kitchen, tennis, and pickleball courts! Come visit to see if Central Parc is the perfect community for you!

4607 Schubert Trail, North Port

Listing courtesy of DR HORTON REALTY SW FL LLC. 239-338-8986

$329,900
3 Beds 2 Baths N6145004 MLS
Don't miss this opportunity to own the "LARGEST HOME" in this neighborhood with living area sq footage of 1503 sq ft!! (Taken from the builders blue prints and measuring!!) Not only that but the largest 2 car garage!! This garage has an 18 ft wide overhead door (recently replaced) plenty of room for 2 cars or that extra room you are always looking for. This villa home is located in the maintenance free area of Berkshire Place in the "Desirable community of Waterford" and centrally located to everything! Enter into your home thru gated courtyard with block walls, paver brick patio & walkways, lovely breakfast/party area with beautiful flowering shrubs, colorful butterflies giving pleasure for all. This home is located at the end of the street on the cul-de-sac and gives lots of extra room for your everyday living pleasure AND extra parking for guests! Privacy is at a premium for this lot, the street backs to the county/city park with hundreds of acres of wooded land and walking trails. Then, your home backs to a picturesque small lake/pond with lots of beautiful birds and wildlife then on to the golf course! Next, thru the front door into a "great room" design that is very open and light with volume ceilings, ceiling fans, lots of light from that beautiful Florida sunshine. Choices of location for dining and living then out to a screen lanai for your morning coffee, afternoon cocktail or maybe a nice quiet reading area. Lanai overlooks the lake/pond, then out to the golf course giving long panoramic view of all. Master bed room is spacious w/ensuite bathroom and walkin closet along w/ water/golf course views. Home is a split bedroom plan giving privacy to all. Bedroom 2 is centrally located and has multiple choices of use, office, den, man cave, the list goes on. Laundry is located inside and is very handy and accommodating for all. Bed room 3 is nicely located with sliding glass doors to your outside patio/party area and gives a nice private entry when needed along with your own "PRIVATE door into garage!! THEN the Kitchen! Probably the busiest room in the house, nice and roomy with multiple cabinets, storage, great pullout drawers in all cabinets then complimented with granite counters and backsplash. Handy breakfast area for your morning paper, Vinyl flooring then out to the courtyard patio thru double sliding glass doors. Home is complimented with laminate and vinyl flooring thru out except Bedroom 2 has carpet. Tile roof was new in 2025, exterior paint 2024, Air conditioner 2021 and newer 18 ft garage door, etc. Location is second to none!! Within minutes to Historical Downtown Venice for your shopping and dining pleasures and on the Gulf of Mexico for some of the finest beaches for your everyday pleasure PLUS the Intracoastal Waterway gives you access for your boating delights!

1275 Berkshire Circle, Venice

Listing courtesy of RE/MAX ALLIANCE GROUP. 941-486-8686

$650,000
4 Beds 4 Baths A4691535 MLS
Investor / Builder Alert! Exceptional WEST OF TRAIL opportunity in one of Sarasota’s desirable neighborhoods, Poinsettia Park. Located just steps from top-rated Southside Elementary School, this property offers incredible potential for redevelopment. The existing structure is a grandfathered duplex that is in very poor condition and best suited for teardown. The true value lies in the land — a 50’ x 118’ lot ideally positioned for a stunning new custom home. But if you prefer, you can keep it as a duplex and rent it. Consider it a blank canvas. Located within the city limits so short term rentals are acceptable. Enjoy a highly sought-after location just minutes to the shops and dining of Southside Village, the world-renowned beaches of Siesta Key, and the vibrant arts, dining, and waterfront lifestyle of Downtown Sarasota. Whether you’re a builder, investor, or end user looking to create a dream home, this is a rare chance to build new in an established, high-demand area surrounded by luxury properties. Opportunities like this are becoming increasingly scarce—don’t miss your chance to capitalize on this premium location! Sold as is with right to inspect.

1824 Webber Street, Central Sarasota

Listing courtesy of RE/MAX ALLIANCE GROUP. 941-954-5454

$1,895,000
4 Beds 4 Baths GC539589 MLS
A rare blend of modern luxury, income potential + lifestyle flexibility awaits in this striking custom 2023 duplex in the heart of Gillespie Park, moments from downtown Sarasota. Designed for those wanting more than just a home, this architectural standout offers 4,400+ sq ft of elevated living with two fully independent residences, each approx 2,200 sq ft featuring 2 bedrooms, 2 bathrooms, private laundry, soaring ceilings + a light-filled expansive design. Whether downsizing, creating a multi-gen retreat, or offsetting your lifestyle with income, this property delivers exceptional versatility, live in one + generate revenue from the other (currently $3,600/month). The main level showcases a chef-inspired kitchen with premium Thermador appliances, gas cooking, dual dishwashers, walk-in pantry + built-in coffee/wine bar, while the upper level offers a refined private living experience with sleek Bosch appliances+ ensuite bedrooms. Outdoor living feels like a private resort with a secluded courtyard featuring an outdoor kitchen and hot tub, plus an expansive second-level balcony ideal for relaxing. Built for efficiency + longevity with solar power, natural gas tankless water heaters, elevator access + rare 3-car alley-access garage, features seldom found this close to downtown. Zoned for short-term rentals and crafted as a high-end multigenerational retreat with full custom handicap-accessible design, delivering an exclusive lifestyle in a prime location.

1755 7th Street, North Sarasota

Listing courtesy of DANIEL CRAPPS AGENCY, INC.. 386-755-5110

$215,000
2 Beds 2 Baths A4684564 MLS 5061 BLDG.
(RENT TO OWN OPTION AVAILABLE, 10K DOWN, PORTION OF RENT GOES TO PRINCIPLE. PLEASE INQUIRE FOR MORE DETAILS. GOOD CREDIT AND JOB REQUIRED.) All the upgrades added in this renovation! Luxurious living at an affordable price (reduced again to encourage offers!) less than a mile from FSU Center for Performing Arts, Ringling Museum, New World College, Asolo Theater, and SRQ (10 minutes to downtown, 15 minutes to St Armand’s Circle/Lido Key Beach, 20 minutes to Siesta Key)! This condo has been renovated beyond the usual with perks like a new reverse osmosis water system in the kitchen and water filters on both showers and bathroom sinks. There are also high-end, first-class touches like seagrass wallpaper and crown molding and gorgeous quartz countertops! Tucked into the desirable Barrington Woods (gated) complex, this is a great location for a fraction of what you would pay for a comparable unit just a couple of miles south in downtown. New hurricane windows, freshly painted interior and exterior. New roof in 2022. New A/C unit in 2022. Lots of natural light. Kitchen: new marbled quartz countertops, stylish white cabinets, new stainless double sink with disposal, new faucet fixtures, new reverse osmosis tankless water filtration system, lots of cabinets and a pantry for storage. Stainless refrigerator, glass-top stove, dishwasher. Bathrooms: new fixtures, gorgeous Victorian wooden vanities, multi-layered filtration systems on sinks so you can brush your teeth and wash your face with the cleanest water as well as shower heads. There is also a versatile Florida room (aka lanai) is fully enclosed with big sliding glass windows overlooking new landscaping (palm trees and flowers) with a new tropical ceiling fan. Gorgeous easy to care for gray waterproof laminate wood floors throughout the unit. Large family room open area for couches, tables, dining, whatever. Front-loading large-capacity washer and dryer in their own closeted area with storage shelves above. Large primary suite with walk-in closet, new stylish barn door to bath and dressing area, Charming guest bedroom with seagrass wallpaper, crown molding, baseboards and decorative piping on the walls. Front porch big enough for sitting or for large potted plants. Outdoor storage closet (that locks securely) for storing your gardening tools or your beach chairs or bicycle. Lawn maintenance is included. Sprinkler system and drip lines for landscaping. Sparkling pool just across the quaint wooden pedestrian bridge over the lake where birds and turtles frolic. Your own parking space in front of the unit under the cover of a carport. Plenty of guest parking available nearby. Pets allowed up to 40 lbs. Move-in ready. Furnished or not (or partial).

5061 Barrington Circle Unit 1302, North Sarasota

Listing courtesy of REALNET FLORIDA REAL ESTATE. greg.vanderwel@realnettampabay.com

$1,100,000
4 Beds 3 Baths A4672875 MLS
Under Construction. **New Construction Luxury Half Duplex in Gillespie Park – Walkable to Downtown Sarasota** Discover a rare opportunity to own a newly constructed luxury residence in Sarasota's highly sought-after Historic Gillespie Park neighborhood. This three-story, all-block half duplex offers more than 2,500 square feet of thoughtfully designed living space, featuring 4 bedrooms, 3 bathrooms, a spacious third-floor flex room, and an expansive rooftop-style balcony ideal for entertaining, working remotely, or enjoying Sarasota's year-round sunshine. Currently in the drywall phase of construction, this home presents a unique chance for buyers to personalize interior finishes, fixtures, and materials before completion. Major infrastructure is already in place, including electrical, plumbing, hurricane-rated PGT impact windows, and a durable EPDM roofing system. The versatile third-floor space can serve as a home office, media room, game room, art studio, fitness area, or private retreat. Located just four homes from Gillespie Park and only blocks from Downtown Sarasota, residents will enjoy convenient access to award-winning restaurants, boutique shopping, cultural venues, theaters, farmers markets, waterfront attractions, and the vibrant downtown lifestyle that makes Sarasota one of Florida's most desirable places to live. Priced at $1.1 million, this property offers the rare combination of new construction, customizable finishes, modern hurricane-resistant construction, and an unbeatable walkable location near downtown Sarasota. **Important:** This offering is for the west-side residence only. The property is currently situated on a single parcel. Sale is contingent upon final municipal approval, recording of the lot split, and issuance of a separate Parcel ID prior to closing. Schedule your private tour today and secure one of the most unique new construction opportunities currently available in Gillespie Park and Downtown Sarasota.

1755 8th Street Unit West, North Sarasota

Listing courtesy of WAGNER REALTY. 941-727-2800

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