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TURNKEY FURNISHED, INCOME-PRODUCING SARASOTA POOL HOME! Discover an exceptional investment opportunity with this beautifully updated 3-bedroom, 2-bath residence offering 1,915 square feet of living space on an expansive .36-ACRE LOT! Currently operating as a successful vacation rental with over $72,000 in gross rental bookings for Jan-Dec 2026, this property offers an attractive opportunity for investors looking to expand their portfolio, while also serving as an ideal seasonal retreat or year-round residence. With no mandatory HOA fees or HOA rental restrictions, this home offers flexibility for its next owner. Step inside to an inviting split-bedroom floor plan featuring vinyl flooring throughout the main living areas, an updated kitchen with granite countertops, modern cabinetry, and stainless steel appliances, along with updated bathrooms and a dedicated laundry room. The spacious primary suite features a private ensuite bathroom and walk-in closet, offering a comfortable retreat. Major improvements include a new roof (2021), HVAC system (2025), impact-resistant windows, and an impact-rated garage door, providing added peace of mind and long-term value. The true highlight of this property is the incredible outdoor living space! Step outside to your own private backyard oasis featuring a heated swimming pool, a screened pool enclosure updated in 2021, and an elegant pine wood ceiling accent over the covered lanai. Enjoy outdoor dining with seating for eight, additional lounge areas, and plenty of space to relax or entertain. The fully fenced backyard sits on an oversized .36-acre lot, offering exceptional room to further enhance the outdoor experience with additional recreational amenities, games, or entertaining areas. The attached two-car garage features a 2023 mini-split A/C system and is currently utilized as a recreational and game room, providing additional versatility. Conveniently located near Downtown Sarasota, Lido Beach, Siesta Key, Anna Maria Island, Bradenton Beach, and abundant shopping, dining, golf, and entertainment options, this property offers easy access to some of the Gulf Coast's most desirable destinations. Sold completely turnkey furnished, including furniture, décor, televisions, kitchenware, linens, and outdoor furnishings, this home offers a seamless opportunity for its next owner. Whether you're seeking an established income-producing property, a Florida vacation getaway, or primary residence, this Sarasota pool home delivers an outstanding combination of location, flexibility, and lifestyle!

3 Beds ⋅ 2 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code

TURNKEY FURNISHED, INCOME-PRODUCING SARASOTA POOL HOME! Discover an exceptional investment opportunity with this beautifully updated 3-bedroom, 2-bath residence offering 1,915 square feet of living space on an expansive .36-ACRE LOT! Currently operating as a successful vacation rental with over $72,000 in gross rental bookings for Jan-Dec 2026, this property offers an attractive opportunity for investors looking to expand their portfolio, while also serving as an ideal seasonal retreat or year-round residence. With no mandatory HOA fees or HOA rental restrictions, this home offers flexibility for its next owner. Step inside to an inviting split-bedroom floor plan featuring vinyl flooring throughout the main living areas, an updated kitchen with granite countertops, modern cabinetry, and stainless steel appliances, along with updated bathrooms and a dedicated laundry room. The spacious primary suite features a private ensuite bathroom and walk-in closet, offering a comfortable retreat. Major improvements include a new roof (2021), HVAC system (2025), impact-resistant windows, and an impact-rated garage door, providing added peace of mind and long-term value. The true highlight of this property is the incredible outdoor living space! Step outside to your own private backyard oasis featuring a heated swimming pool, a screened pool enclosure updated in 2021, and an elegant pine wood ceiling accent over the covered lanai. Enjoy outdoor dining with seating for eight, additional lounge areas, and plenty of space to relax or entertain. The fully fenced backyard sits on an oversized .36-acre lot, offering exceptional room to further enhance the outdoor experience with additional recreational amenities, games, or entertaining areas. The attached two-car garage features a 2023 mini-split A/C system and is currently utilized as a recreational and game room, providing additional versatility. Conveniently located near Downtown Sarasota, Lido Beach, Siesta Key, Anna Maria Island, Bradenton Beach, and abundant shopping, dining, golf, and entertainment options, this property offers easy access to some of the Gulf Coast's most desirable destinations. Sold completely turnkey furnished, including furniture, décor, televisions, kitchenware, linens, and outdoor furnishings, this home offers a seamless opportunity for its next owner. Whether you're seeking an established income-producing property, a Florida vacation getaway, or primary residence, this Sarasota pool home delivers an outstanding combination of location, flexibility, and lifestyle!

438 Whitfield Avenue, Sarasota

$499,000

**BRAND NEW ROOF! JUST STEPS FROM SARASOTA BAY!** Discover the possibilities at 139 Adair Avenue, a spacious 3-bedroom, 2.5-bath pool home offering over 2,000 square feet of living space on a quarter-acre lot in the highly desirable Whitfield Estates neighborhood. Located just steps from Sarasota Bay, this property offers an incredible opportunity to create something truly special in one of Sarasota's most established communities. Featuring a generous floor plan, multiple flexible living spaces, and a private screened-in pool, this home offers the space and versatility today's buyers are looking for. An additional bonus room with sliding glass doors provides direct access to the pool and patio, creating a wonderful extension of the home's living and entertaining areas. The primary suite features an adjoining bonus room and additional walk-in closet, offering exciting possibilities for customization, including the potential to reconfigure the space into a fourth bedroom or private guest suite. An additional poolside bathroom space provides even more potential for future improvements. With its substantial square footage, functional layout, and desirable location, this home is a fantastic opportunity for buyers looking to bring their own vision to life. Whether you choose to enjoy the home as it is or transform it with modern updates, the possibilities are endless! Tucked away **WEST OF THE TRAIL** in Whitfield Estates, one of Sarasota's hidden gems, residents enjoy **NO MANDATORY HOA OR CDD FEES** and flexible rental possibilities, including nightly rentals, subject to applicable regulations. Optional membership in the Whitfield Ballentine Manor Association is just $40 annually and includes culinary membership privileges at the prestigious Sara Bay Country Club, currently undergoing an exciting renovation with plans to reopen in 2027. Boating enthusiasts will appreciate nearby Sara Bay Marina, offering convenient access to boat slips and dry storage. Ideally located just minutes from downtown Sarasota, Sarasota Bradenton International Airport, Sarasota Bay, IMG Academy, beautiful Gulf Coast beaches, championship golf, waterfront dining, shopping, and entertainment. Whether you're searching for a spacious primary residence, an investment opportunity, a winter retreat, or the perfect canvas to design your dream home, **139 Adair Avenue offers the space, location, and possibilities to make it your own.** Schedule your private showing today!

3 Beds ⋅ 3 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code

**BRAND NEW ROOF! JUST STEPS FROM SARASOTA BAY!** Discover the possibilities at 139 Adair Avenue, a spacious 3-bedroom, 2.5-bath pool home offering over 2,000 square feet of living space on a quarter-acre lot in the highly desirable Whitfield Estates neighborhood. Located just steps from Sarasota Bay, this property offers an incredible opportunity to create something truly special in one of Sarasota's most established communities. Featuring a generous floor plan, multiple flexible living spaces, and a private screened-in pool, this home offers the space and versatility today's buyers are looking for. An additional bonus room with sliding glass doors provides direct access to the pool and patio, creating a wonderful extension of the home's living and entertaining areas. The primary suite features an adjoining bonus room and additional walk-in closet, offering exciting possibilities for customization, including the potential to reconfigure the space into a fourth bedroom or private guest suite. An additional poolside bathroom space provides even more potential for future improvements. With its substantial square footage, functional layout, and desirable location, this home is a fantastic opportunity for buyers looking to bring their own vision to life. Whether you choose to enjoy the home as it is or transform it with modern updates, the possibilities are endless! Tucked away **WEST OF THE TRAIL** in Whitfield Estates, one of Sarasota's hidden gems, residents enjoy **NO MANDATORY HOA OR CDD FEES** and flexible rental possibilities, including nightly rentals, subject to applicable regulations. Optional membership in the Whitfield Ballentine Manor Association is just $40 annually and includes culinary membership privileges at the prestigious Sara Bay Country Club, currently undergoing an exciting renovation with plans to reopen in 2027. Boating enthusiasts will appreciate nearby Sara Bay Marina, offering convenient access to boat slips and dry storage. Ideally located just minutes from downtown Sarasota, Sarasota Bradenton International Airport, Sarasota Bay, IMG Academy, beautiful Gulf Coast beaches, championship golf, waterfront dining, shopping, and entertainment. Whether you're searching for a spacious primary residence, an investment opportunity, a winter retreat, or the perfect canvas to design your dream home, **139 Adair Avenue offers the space, location, and possibilities to make it your own.** Schedule your private showing today!

139 Adair Avenue, Sarasota

$510,000

PRICE IMPROVED | Income-Producing Golf Course Pool Home at Sara Bay This one is already earning. Set on the 18th hole of Sara Bay Country Club, this 3-bedroom, 2-bath pool home is currently operating as a successful short-term rental, and it has performed well on annual leases too. That gives you flexibility in how you run it. With nearly 2,000 sq. ft. on an oversized .42-acre lot, it's a turnkey investment that can convey fully furnished if desired, so you can step in with income from day one. The covered lanai and sparkling pool look straight out over the fairway to the west, so sunsets are part of the daily routine. The space is private, peaceful, and usable year-round, exactly what guests book for and what you'll want when you're in town yourself. Inside, a split floor plan gives the primary suite and guest rooms their own space. Two living areas add room for hosting, working from home, or giving renters space to spread out. Natural light and thoughtful updates keep the home move-in and rent-ready. The location makes it easy to book and easy to enjoy: about 5 minutes to SRQ Airport, under 15 minutes to downtown Sarasota, and close to beaches, golf, dining, and the arts. Keep it on the short-term calendar, switch to annual tenants, or block off your own winter weeks. It's a vacation home that pays its own way. SELLER INCENTIVE: Seller is offering a 1% closing cost credit or assistance buying down your interest rate. Ask for details.

3 Beds ⋅ 2 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code

PRICE IMPROVED | Income-Producing Golf Course Pool Home at Sara Bay This one is already earning. Set on the 18th hole of Sara Bay Country Club, this 3-bedroom, 2-bath pool home is currently operating as a successful short-term rental, and it has performed well on annual leases too. That gives you flexibility in how you run it. With nearly 2,000 sq. ft. on an oversized .42-acre lot, it's a turnkey investment that can convey fully furnished if desired, so you can step in with income from day one. The covered lanai and sparkling pool look straight out over the fairway to the west, so sunsets are part of the daily routine. The space is private, peaceful, and usable year-round, exactly what guests book for and what you'll want when you're in town yourself. Inside, a split floor plan gives the primary suite and guest rooms their own space. Two living areas add room for hosting, working from home, or giving renters space to spread out. Natural light and thoughtful updates keep the home move-in and rent-ready. The location makes it easy to book and easy to enjoy: about 5 minutes to SRQ Airport, under 15 minutes to downtown Sarasota, and close to beaches, golf, dining, and the arts. Keep it on the short-term calendar, switch to annual tenants, or block off your own winter weeks. It's a vacation home that pays its own way. SELLER INCENTIVE: Seller is offering a 1% closing cost credit or assistance buying down your interest rate. Ask for details.

433 Whitfield Avenue, Sarasota

$5,500,000

Set on a premier waterfront lot in the Sarasota/Bradenton area, this single-family estate offers panoramic water views of Sarasota Bay, a separate guest house / in-law retreat and the kind of indoor-outdoor living buyers expect at the luxury level. The main residence (3806 sq ft) is designed for entertaining and everyday comfort, with expansive living spaces, a well-appointed kitchen, and seamless access to the pool and outdoor areas, while the guest house (2409 sq ft) provides ideal accommodations for visitors, extended family, or a private office retreat. Comfortable luxury living on a combined 1+ acre lot (there are 2 parcels included in this offering) with a spectacular panoramic water view. Beautifully kept grounds accented by Royal palms create the feel of a family compound that elegantly states, "You've made it!" The three-story main house has a twin grand winding staircase and an elevator to the second-floor main level. Tall double-trey ceilings w/ uplighting and massive impact glass windows and doors provide an absolutely breathtaking view of the swimming pool and the Sarasota Bay. Built on 38 concrete and steel reinforced pilings, the main house was constructed in 2001, and the windows and doors were upgraded to hurricane standards. In fact, the owner has a flood policy on the main house for just $1,200 per year. There is an oversized 3 car garage with an expanded work area and 220V power if you have an electric car. Plus, a massive unfinished storage and fun area with non-conforming pool bath below the main living area elevated approximately 18' above. The completely separate guest house also with views of the bay includes an additional 3 bedrooms, great room, dining room, full kitchen, office and attached 2 car garage. The guest house was built in 1950 and remodeled to mimic the Coastal Mediterranean style of the main house. The pool ranges from 3' to 7' in depth and includes remote control lighting and a water feature. The pool and outdoor area create the perfect setting for parties or special events. The pool is surrounded by a huge concrete deck that extends as a patio under the cover of the massive main observation and entertainment deck above. There are rough ins for an outdoor kitchen on the ground floor patio. There is also an additional observation deck off the 3rd floor living room that, with a slight zoom on your camera, provides a nice view of John Ringling bridge. Longboat Key provides night lights beyond the bay, and your own private Osprey nest adds to the natural symphony of life on the water. Boaters, you are less than a mile away from Sara Bay Marina. Commuters, you are less than 3 miles away from SRQ. Beach goers, you are less than 10 miles from Lido Beach and St Armands Circle. Professionals, you are less than 7 miles from downtown Sarasota. Kayakers, walk to the Riprap and launch! Be sure to watch the individual videos showing each interior. They are not just slideshows. This is the first time this property has been offered for sale since the builder owned it. An acre of mainland bayfront land is rare in the Sarasota/Manatee waterfront community. Don't Daydream and miss out on your Dream home. The main home is being sold partially furnished with a few exclusions. The guest house is unfurnished. Capture the Zen of waterfront living for yourself and future generations now.

6 Beds ⋅ 6 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code

Set on a premier waterfront lot in the Sarasota/Bradenton area, this single-family estate offers panoramic water views of Sarasota Bay, a separate guest house / in-law retreat and the kind of indoor-outdoor living buyers expect at the luxury level. The main residence (3806 sq ft) is designed for entertaining and everyday comfort, with expansive living spaces, a well-appointed kitchen, and seamless access to the pool and outdoor areas, while the guest house (2409 sq ft) provides ideal accommodations for visitors, extended family, or a private office retreat. Comfortable luxury living on a combined 1+ acre lot (there are 2 parcels included in this offering) with a spectacular panoramic water view. Beautifully kept grounds accented by Royal palms create the feel of a family compound that elegantly states, "You've made it!" The three-story main house has a twin grand winding staircase and an elevator to the second-floor main level. Tall double-trey ceilings w/ uplighting and massive impact glass windows and doors provide an absolutely breathtaking view of the swimming pool and the Sarasota Bay. Built on 38 concrete and steel reinforced pilings, the main house was constructed in 2001, and the windows and doors were upgraded to hurricane standards. In fact, the owner has a flood policy on the main house for just $1,200 per year. There is an oversized 3 car garage with an expanded work area and 220V power if you have an electric car. Plus, a massive unfinished storage and fun area with non-conforming pool bath below the main living area elevated approximately 18' above. The completely separate guest house also with views of the bay includes an additional 3 bedrooms, great room, dining room, full kitchen, office and attached 2 car garage. The guest house was built in 1950 and remodeled to mimic the Coastal Mediterranean style of the main house. The pool ranges from 3' to 7' in depth and includes remote control lighting and a water feature. The pool and outdoor area create the perfect setting for parties or special events. The pool is surrounded by a huge concrete deck that extends as a patio under the cover of the massive main observation and entertainment deck above. There are rough ins for an outdoor kitchen on the ground floor patio. There is also an additional observation deck off the 3rd floor living room that, with a slight zoom on your camera, provides a nice view of John Ringling bridge. Longboat Key provides night lights beyond the bay, and your own private Osprey nest adds to the natural symphony of life on the water. Boaters, you are less than a mile away from Sara Bay Marina. Commuters, you are less than 3 miles away from SRQ. Beach goers, you are less than 10 miles from Lido Beach and St Armands Circle. Professionals, you are less than 7 miles from downtown Sarasota. Kayakers, walk to the Riprap and launch! Be sure to watch the individual videos showing each interior. They are not just slideshows. This is the first time this property has been offered for sale since the builder owned it. An acre of mainland bayfront land is rare in the Sarasota/Manatee waterfront community. Don't Daydream and miss out on your Dream home. The main home is being sold partially furnished with a few exclusions. The guest house is unfurnished. Capture the Zen of waterfront living for yourself and future generations now.

7524 Westmoreland Drive, Sarasota

$540,000

Welcome to this charming mid-century Florida rancher nestled in the sought-after waterfront neighborhood of Whitfield Estates — one of Sarasota's most beloved and established communities. Set on a generous 0.29-acre corner lot, this 2-bedroom, 2-bathroom home offers 1,371 square feet of comfortable living space with genuine Florida character and serious income-producing potential. Whether you're searching for a personal retreat or a turnkey investment, this home delivers. Currently active on Airbnb and generating approximately $180 per night, it has already proven itself as a strong short-term rental performer — making it an exceptional opportunity for investors looking to capitalize on Sarasota's thriving tourism market. Inside, you'll find renovated bathrooms that bring a fresh, modern touch to the home's classic bones. The layout is bright and functional, with a warm, welcoming feel that guests and homeowners alike will appreciate. Step outside and enjoy everything that comes with life in Whitfield Estates — a peaceful, established neighborhood with a true sense of community, no HOA, and easy access to the very best of Sarasota. World-renowned Siesta Key Beach, the cultural richness of downtown Sarasota, St. Armands Circle shopping, and the Ringling Museum are all just minutes away. No HOA. Corner lot. Proven rental income. And all the Florida sunshine you could ask for. Offered at $570,000.

2 Beds ⋅ 2 Baths ⋅ Whitfield Estates SubDv. ⋅ 34243 Zip Code

Welcome to this charming mid-century Florida rancher nestled in the sought-after waterfront neighborhood of Whitfield Estates — one of Sarasota's most beloved and established communities. Set on a generous 0.29-acre corner lot, this 2-bedroom, 2-bathroom home offers 1,371 square feet of comfortable living space with genuine Florida character and serious income-producing potential. Whether you're searching for a personal retreat or a turnkey investment, this home delivers. Currently active on Airbnb and generating approximately $180 per night, it has already proven itself as a strong short-term rental performer — making it an exceptional opportunity for investors looking to capitalize on Sarasota's thriving tourism market. Inside, you'll find renovated bathrooms that bring a fresh, modern touch to the home's classic bones. The layout is bright and functional, with a warm, welcoming feel that guests and homeowners alike will appreciate. Step outside and enjoy everything that comes with life in Whitfield Estates — a peaceful, established neighborhood with a true sense of community, no HOA, and easy access to the very best of Sarasota. World-renowned Siesta Key Beach, the cultural richness of downtown Sarasota, St. Armands Circle shopping, and the Ringling Museum are all just minutes away. No HOA. Corner lot. Proven rental income. And all the Florida sunshine you could ask for. Offered at $570,000.

138 Pearl Avenue, Sarasota

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