Rare corner-lot duplex in Sarasota’s highly desirable Laurel Park Historic District, located approximately 0.5 miles from downtown Sarasota’s dining, shopping, arts, bayfront, and cultural attractions. Set beneath mature trees and surrounded by the timeless character of Laurel Park, this well-maintained property blends classic Old Florida charm with substantial recent improvements. Each residence offers 2 bedrooms, 1 bathroom, spacious living areas, a full kitchen, a dedicated laundry area, and its own private screened lanai overlooking fully fenced outdoor spaces that provide privacy and separation between the units. Recent improvements include a new roof installed in November 2024, new windows installed in September 2022, a full exterior repaint completed in January 2025, a remodeled bathroom, custom paver hardscaping, and refreshed landscaping. One residence also features a private putting green, a distinctive outdoor amenity rarely found near downtown Sarasota. Laurel Park is known for its historic character and convenient proximity to Burns Court, Payne Park, downtown Sarasota, and Sarasota Bay. Lido Key and Siesta Key beaches are also just a short drive away. Whether used as an owner-occupied residence with supplemental rental income, a long-term investment property, or a flexible downtown retreat, this duplex offers a variety of possibilities in one of Sarasota’s most charming and centrally located neighborhoods. An exceptional opportunity to own a versatile property offering character, privacy, recent improvements, and an outstanding downtown Sarasota location.

4 Beds ⋅ 2 Baths ⋅ A4701927 MLS

Rare corner-lot duplex in Sarasota’s highly desirable Laurel Park Historic District, located approximately 0.5 miles from downtown Sarasota’s dining, shopping, arts, bayfront, and cultural attractions. Set beneath mature trees and surrounded by the timeless character of Laurel Park, this well-maintained property blends classic Old Florida charm with substantial recent improvements. Each residence offers 2 bedrooms, 1 bathroom, spacious living areas, a full kitchen, a dedicated laundry area, and its own private screened lanai overlooking fully fenced outdoor spaces that provide privacy and separation between the units. Recent improvements include a new roof installed in November 2024, new windows installed in September 2022, a full exterior repaint completed in January 2025, a remodeled bathroom, custom paver hardscaping, and refreshed landscaping. One residence also features a private putting green, a distinctive outdoor amenity rarely found near downtown Sarasota. Laurel Park is known for its historic character and convenient proximity to Burns Court, Payne Park, downtown Sarasota, and Sarasota Bay. Lido Key and Siesta Key beaches are also just a short drive away. Whether used as an owner-occupied residence with supplemental rental income, a long-term investment property, or a flexible downtown retreat, this duplex offers a variety of possibilities in one of Sarasota’s most charming and centrally located neighborhoods. An exceptional opportunity to own a versatile property offering character, privacy, recent improvements, and an outstanding downtown Sarasota location.

507 Madison Court, Downtown

Listing courtesy of EXP REALTY LLC. 888-883-8509

$749,000

Under contract-accepting backup offers. * Tremendous opportunity to own your own duplex in GILLESPIE PARK – LIVE IN ONE SIDE AND RENT OUT THE OTHER ! Or just rent out both of them ! * Fabulous opportunity to tear down and build your own New Single Family Home in the Downtown area with an Additional Dwelling unit for Income – Zoned DTN + During the time of preparing all the Architectural plans and going through the permitting process – you are collecting rent all along the way ! * You could even add a pool between the 2 New Buildings for Fun for all ! *Right across street from Sarasota’s Own 10 acre Wooded Oasis in the middle of Downtown Sarasota – GILLESPIE PARK ! Featuring Tennis Courts , walking trails , a pond that winds through the park , Wonderful playground and even a separate Dog Park ! * Tenant occupied* There is total of 3 br, 2 bath. (one unit has 2 br, 1 bath, and one unit has 1 br, 1 bath) *To have access to all that Downtown Sarasota has to offer within just a few blocks is amazing ! You literally have 65 restaurants within a 10 block radius. Who needs a car anyway ? * The Bay Trolley is just a few blocks away as well taking you all the way to Lido Beach and back for Free without ever having to park a car! * And Don’t Forget the ever popular Legacy Walking and Bicycle Trail and Payne Park also just a few blocks away. * And One Last Huge Benefit - You are literally only 6 blocks from the Ultra Amazing new 53 acre Bay Park ! Which you just have to see and experience to believe. *YOU must experience the Downtown Lifestyle to really appreciate what our Great City has to offer !

3 Beds ⋅ 2 Baths ⋅ A4699425 MLS

Under contract-accepting backup offers. * Tremendous opportunity to own your own duplex in GILLESPIE PARK – LIVE IN ONE SIDE AND RENT OUT THE OTHER ! Or just rent out both of them ! * Fabulous opportunity to tear down and build your own New Single Family Home in the Downtown area with an Additional Dwelling unit for Income – Zoned DTN + During the time of preparing all the Architectural plans and going through the permitting process – you are collecting rent all along the way ! * You could even add a pool between the 2 New Buildings for Fun for all ! *Right across street from Sarasota’s Own 10 acre Wooded Oasis in the middle of Downtown Sarasota – GILLESPIE PARK ! Featuring Tennis Courts , walking trails , a pond that winds through the park , Wonderful playground and even a separate Dog Park ! * Tenant occupied* There is total of 3 br, 2 bath. (one unit has 2 br, 1 bath, and one unit has 1 br, 1 bath) *To have access to all that Downtown Sarasota has to offer within just a few blocks is amazing ! You literally have 65 restaurants within a 10 block radius. Who needs a car anyway ? * The Bay Trolley is just a few blocks away as well taking you all the way to Lido Beach and back for Free without ever having to park a car! * And Don’t Forget the ever popular Legacy Walking and Bicycle Trail and Payne Park also just a few blocks away. * And One Last Huge Benefit - You are literally only 6 blocks from the Ultra Amazing new 53 acre Bay Park ! Which you just have to see and experience to believe. *YOU must experience the Downtown Lifestyle to really appreciate what our Great City has to offer !

1850 7th Street, Downtown

Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY. 941-364-4000

$2,529,000

SARASOTA ~ CITY OF SARASOTA ~ ROSEMARY DISTRICT ~ DOWNTOWN LIVING AND / OR INVESTMENT, WITH UPSIDE DEVELOPMENT OPPORTUNITIES! - WE ARE SELLING 4 CONTIGUOUS PROPERTIES WITH FOUR RENTAL HOMES ON AN ESTIMATED 23K SF +/- LAND!!!! Come and explore this unique opportunity to own and operate four contiguous properties with homes within the much sought after City of Sarasota "Rosemary District". The current rent roll is estimated at $100K +/-, all the current homes (4) are rented on an annual basis. The zoning does allow for short term weekly rentals, come and set up your own short term rental compound with estimated average daily rates @ $50.00 - $100.00 +/. Want another reason to look, owner will consider "owner financing" and/or selling off less then all four homes. There are just not many opportunities in the City of Sarasota to secure rezoned lands with the ability to use the current as-is property to secure carry income while waiting for the right timing to develop. The upside development in the Rosemary Zoning District: up to 7-stories with up to 30+ units. Property is very easy to show, sign is on site! NOTE: another contiguous parcel - rental home available for discussion. NOTE: future development plans viable on request!

32 Beds ⋅ 16 Baths ⋅ A4699070 MLS ⋅ 1555/1551/1569/1563 BLDG.

SARASOTA ~ CITY OF SARASOTA ~ ROSEMARY DISTRICT ~ DOWNTOWN LIVING AND / OR INVESTMENT, WITH UPSIDE DEVELOPMENT OPPORTUNITIES! - WE ARE SELLING 4 CONTIGUOUS PROPERTIES WITH FOUR RENTAL HOMES ON AN ESTIMATED 23K SF +/- LAND!!!! Come and explore this unique opportunity to own and operate four contiguous properties with homes within the much sought after City of Sarasota "Rosemary District". The current rent roll is estimated at $100K +/-, all the current homes (4) are rented on an annual basis. The zoning does allow for short term weekly rentals, come and set up your own short term rental compound with estimated average daily rates @ $50.00 - $100.00 +/. Want another reason to look, owner will consider "owner financing" and/or selling off less then all four homes. There are just not many opportunities in the City of Sarasota to secure rezoned lands with the ability to use the current as-is property to secure carry income while waiting for the right timing to develop. The upside development in the Rosemary Zoning District: up to 7-stories with up to 30+ units. Property is very easy to show, sign is on site! NOTE: another contiguous parcel - rental home available for discussion. NOTE: future development plans viable on request!

1555 7th Street, Downtown

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

$2,995,000

One of the Last Remaining Legacy Properties on Golden Gate Point | Rare Trophy Ownership, Redevelopment & Strategic Hold Opportunity A truly rare offering in one of Sarasota’s most exclusive and rapidly evolving luxury enclaves. With no true single-family homes currently remaining on Golden Gate Point and only a small handful of original legacy properties left, 161 Golden Gate Point represents one of the final opportunities to control a meaningful piece of “old Golden Gate” before the peninsula is fully transformed. Positioned in the heart of downtown Sarasota, across from the Ritz-Carlton and adjacent to Marina Jack, the property currently consists of a fully updated Four-unit building featuring newer central A/Cs, five-piece stainless kitchens, quartz countertops, new roof (2025), separate electrical meters, gated courtyards, hot tub, and gazebo — offering immediate usability and meaningful interim income while future plans are explored. Located within the City of Sarasota weekly vacation rental zone, this creates a rare opportunity not commonly found in downtown Sarasota — operate the property similarly to a boutique hotel. For the visionary buyer, this may represent a once-in-a-generation opportunity to create what could become Golden Gate Point’s only true single-family estate — a one-of-one trophy residence in the heart of downtown Sarasota. The property also presents compelling redevelopment potential. Golden Gate Point benefits from alternative development standards intended to support a more urban, pedestrian-friendly environment, including reduced setbacks, increased building coverage allowances, and flexible dimensional standards — enhancing redevelopment possibilities in this highly sought-after peninsula location. Similar RMF-5 sites on Golden Gate Point have supported boutique luxury residential concepts, while the adjacent rear assemblage totaling approximately 21,600 SF is also available, creating a rare opportunity for a larger strategic assemblage in one of Sarasota’s most supply-constrained luxury micro-markets. 161 also represents a compelling long-term hold opportunity. As Golden Gate Point continues its luxury transformation — and remaining legacy properties disappear — the opportunity to control irreplaceable downtown Sarasota land becomes increasingly rare. Just moments to Marina Jack, downtown Sarasota dining, St. Armands Circle, Lido Beach, and Sarasota’s transformative bayfront destination, The Bay. Whether envisioned as: • Rare short-term rental building where you control the entire property • One of Golden Gate Point’s final legacy holdings • A future one-of-one single-family estate • A boutique luxury redevelopment site • A strategic assemblage opportunity • A family office or long-term scarcity hold • Or a rare downtown Sarasota land play with meaningful interim income potential …opportunities of this nature are becoming increasingly difficult to replicate.

4 Beds ⋅ 4 Baths ⋅ A4696009 MLS

One of the Last Remaining Legacy Properties on Golden Gate Point | Rare Trophy Ownership, Redevelopment & Strategic Hold Opportunity A truly rare offering in one of Sarasota’s most exclusive and rapidly evolving luxury enclaves. With no true single-family homes currently remaining on Golden Gate Point and only a small handful of original legacy properties left, 161 Golden Gate Point represents one of the final opportunities to control a meaningful piece of “old Golden Gate” before the peninsula is fully transformed. Positioned in the heart of downtown Sarasota, across from the Ritz-Carlton and adjacent to Marina Jack, the property currently consists of a fully updated Four-unit building featuring newer central A/Cs, five-piece stainless kitchens, quartz countertops, new roof (2025), separate electrical meters, gated courtyards, hot tub, and gazebo — offering immediate usability and meaningful interim income while future plans are explored. Located within the City of Sarasota weekly vacation rental zone, this creates a rare opportunity not commonly found in downtown Sarasota — operate the property similarly to a boutique hotel. For the visionary buyer, this may represent a once-in-a-generation opportunity to create what could become Golden Gate Point’s only true single-family estate — a one-of-one trophy residence in the heart of downtown Sarasota. The property also presents compelling redevelopment potential. Golden Gate Point benefits from alternative development standards intended to support a more urban, pedestrian-friendly environment, including reduced setbacks, increased building coverage allowances, and flexible dimensional standards — enhancing redevelopment possibilities in this highly sought-after peninsula location. Similar RMF-5 sites on Golden Gate Point have supported boutique luxury residential concepts, while the adjacent rear assemblage totaling approximately 21,600 SF is also available, creating a rare opportunity for a larger strategic assemblage in one of Sarasota’s most supply-constrained luxury micro-markets. 161 also represents a compelling long-term hold opportunity. As Golden Gate Point continues its luxury transformation — and remaining legacy properties disappear — the opportunity to control irreplaceable downtown Sarasota land becomes increasingly rare. Just moments to Marina Jack, downtown Sarasota dining, St. Armands Circle, Lido Beach, and Sarasota’s transformative bayfront destination, The Bay. Whether envisioned as: • Rare short-term rental building where you control the entire property • One of Golden Gate Point’s final legacy holdings • A future one-of-one single-family estate • A boutique luxury redevelopment site • A strategic assemblage opportunity • A family office or long-term scarcity hold • Or a rare downtown Sarasota land play with meaningful interim income potential …opportunities of this nature are becoming increasingly difficult to replicate.

161 Golden Gate Point, Downtown

Listing courtesy of AMY ROBINSON REAL ESTATE LLC. 941-346-7000

$999,000

Prime Investment Opportunity in Laurel Park – Fabulous 4-Plex with Exceptional Income Potential! Discover your next smart investment in the heart of Laurel Park, one of Sarasota’s most desirable and historic neighborhoods. Just three blocks from vibrant Main Street and minutes from the city’s renowned Gulf Coast beaches, this charming 4-unit multifamily property offers a rare chance to own premium real estate in a high demand location. The property consists of two separate buildings, each featuring an upper and lower 1-bedroom, 1-bath apartment, with ample off-street parking for tenants. All units are currently leased to reliable annual tenants, ensuring immediate income. For investors seeking to maximize returns, this property offers significant upside as a short-term rental, with the potential to generate substantially higher income through weekly bookings in a vacation-friendly market.

4 Beds ⋅ 4 Baths ⋅ A4680127 MLS

Prime Investment Opportunity in Laurel Park – Fabulous 4-Plex with Exceptional Income Potential! Discover your next smart investment in the heart of Laurel Park, one of Sarasota’s most desirable and historic neighborhoods. Just three blocks from vibrant Main Street and minutes from the city’s renowned Gulf Coast beaches, this charming 4-unit multifamily property offers a rare chance to own premium real estate in a high demand location. The property consists of two separate buildings, each featuring an upper and lower 1-bedroom, 1-bath apartment, with ample off-street parking for tenants. All units are currently leased to reliable annual tenants, ensuring immediate income. For investors seeking to maximize returns, this property offers significant upside as a short-term rental, with the potential to generate substantially higher income through weekly bookings in a vacation-friendly market.

301 S Osprey Avenue, Downtown

Listing courtesy of QUEST PROPERTIES INC. 941-504-1111

$1,159,999

FIVE UNIT APARTMENT COMPLEX. DTN zoned corner lot in downtown Sarasota. Fully rented month to month annual agreements paying below market value, 3 are month to month and 2 have a 1 year lease. City zoning allows weekly rentals. Purchase and earn rental income OR develop in DTN zoning. Common area laundry as an amenity for tenants. Bldg #1 has 2 units, each are 1 bedroom/1 bath. Bldg 2 has 2 units, each are 2 bedroom/1 bath. Bldg #3 is the cottage/studio. This property is in fast growing downtown Sarasota a few blocks to Main Street with downtown restaurants, shops and bars. 2 blocks from Sarasota City park with tennis courts, playground and dog park all situated around a lake! Many multimillion dollar homes and deluxe condo developments in and surrounding Gillespie Park. Close to beaches and beautiful Sarasota Bay. Investment property with huge income potential and huge future DTN development. Seller is offering owner/seller financing to prospective buyers in the amount of 40% of purchase price. All financing terms are extremely attractive. Minimum balloon options will be considered. Seller will not go into 2nd position as lender.

6 Beds ⋅ 5 Baths ⋅ A4674885 MLS

FIVE UNIT APARTMENT COMPLEX. DTN zoned corner lot in downtown Sarasota. Fully rented month to month annual agreements paying below market value, 3 are month to month and 2 have a 1 year lease. City zoning allows weekly rentals. Purchase and earn rental income OR develop in DTN zoning. Common area laundry as an amenity for tenants. Bldg #1 has 2 units, each are 1 bedroom/1 bath. Bldg 2 has 2 units, each are 2 bedroom/1 bath. Bldg #3 is the cottage/studio. This property is in fast growing downtown Sarasota a few blocks to Main Street with downtown restaurants, shops and bars. 2 blocks from Sarasota City park with tennis courts, playground and dog park all situated around a lake! Many multimillion dollar homes and deluxe condo developments in and surrounding Gillespie Park. Close to beaches and beautiful Sarasota Bay. Investment property with huge income potential and huge future DTN development. Seller is offering owner/seller financing to prospective buyers in the amount of 40% of purchase price. All financing terms are extremely attractive. Minimum balloon options will be considered. Seller will not go into 2nd position as lender.

503 N Osprey Avenue, Downtown

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

$3,899,000

Pre-Construction. To be built. INVESTOR - DEVELOPER OPPORTUNITY in Rosemary District on Orange Ave! Three Lots permitted for five story, 18 unit condos. Orange Ave is a thriving corridor from Downtown to Rosemary with recently finished projects with this one to be a highlight to the street. Flanked by the Sarasota Military Academy to the North and Citrus Square to the South, this opportunity is positioned in a spectacular and convenient location. Distance to Main St - Downtown 0.4 miles Distance to Sarasota Airport (SRQ) 3.8 miles Distance to Ringling College 1.7 miles The prime benefit to buyer is “time”, team has worked for over a year and have APPROVED Civil Plans from City of Sarasota and development team is working on construction drawings to be submitted for approval, this project is 60-90 days away from shovel ready.

A4671980 MLS

Pre-Construction. To be built. INVESTOR - DEVELOPER OPPORTUNITY in Rosemary District on Orange Ave! Three Lots permitted for five story, 18 unit condos. Orange Ave is a thriving corridor from Downtown to Rosemary with recently finished projects with this one to be a highlight to the street. Flanked by the Sarasota Military Academy to the North and Citrus Square to the South, this opportunity is positioned in a spectacular and convenient location. Distance to Main St - Downtown 0.4 miles Distance to Sarasota Airport (SRQ) 3.8 miles Distance to Ringling College 1.7 miles The prime benefit to buyer is “time”, team has worked for over a year and have APPROVED Civil Plans from City of Sarasota and development team is working on construction drawings to be submitted for approval, this project is 60-90 days away from shovel ready.

711 N Orange Avenue, Downtown

Listing courtesy of WAGNER REALTY. 941-727-2800

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