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Trail Acres Naples Florida Homes for Sale

Naples Florida Real Estate

Trail Acres Naples Real Estate

Homes For Sale3$310K - $460K
Land For Sale3$149K - $825K
Sold ( Past 6 Months )5$240K - $636K
Last updated at 1:55pm 08/07/2026

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$459,900
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Trail Acres

281 Benson St E, Naples, FL 34113

Homes - 1,552 ft² / 2,134 ft² - 1 Car Garage - 1 Carport

3+Den / 3 Baths

Built 1992
Trail Acres Naples Homes for Sale: This is a nice property, specially for first time home buyer and investors, very spacious with extra space for a bigger family. This property was updated about 1 year ago with mostly everything. located very close the Marci Iland , minute away from everything.



$395,000
Decrease*
$20K
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Trail Acres

224 Benson St, Naples, FL 34113

Homes - 1,333 ft² / 1,578 ft² - 1 Car Garage

3 Bed / 2 Baths

Built 1994
Trail Acres Naples Homes for Sale: One or more photo(s) has been virtually staged, AI generated or rendered. BOTANICAL PARADISE MEETS KEY WEST CHARM IN THE HEART OF NAPLES Tucked away in the welcoming community of Trail Acres, this truly one-of-a-kind Key West-inspired residence offers a rare combination of tropical beauty, exceptional efficiency, and easy Florida living. Situated on a beautifully landscaped homesite, the backyard is nothing short of a botanist's dream, showcasing more than 100 species of plants, mature fruit-bearing trees, vibrant rock gardens, aloe plantings, and thoughtfully designed outdoor living spaces that create your own private tropical retreat. Designed to embrace the Florida lifestyle, the outdoor amenities are exceptional. Enjoy a covered front porch, screened lanai for year-round dining and relaxation, and a charming 10' x 10' screened Chickee Hut with thatched roof handcrafted by local Seminole artisans. The fenced backyard also features solar-powered landscape lighting, ten rainwater collection barrel systems, a storage shed, chicken coop, and numerous garden areas perfect for gardening enthusiasts or anyone seeking a peaceful outdoor sanctuary. Built for both comfort and peace of mind, this home is equipped with Bahama hurricane shutters, remote-controlled roll-down metal storm shutters, a low-maintenance white metal roof, and a 2021 Trane HVAC system. Inside, all living areas are conveniently located on one level. The entry foyer opens to a comfortable living room with abundant natural light and hurricane-protected windows. The bright kitchen offers white cabinetry, white appliances, a sunny breakfast area, and sliding glass doors leading directly to the screened lanai—perfect for seamless indoor-outdoor entertaining. The primary suite features a walk-in closet and private en-suite bath. Two additional bedrooms each include walk-in closets with custom built-ins and hurricane shutters, providing flexibility for family, guests, or a home office. Additional highlights include a one-car front-loading garage complete with storage loft and laundry loft, a paver and gravel driveway accommodating up to four vehicles, public water and sewer, central air conditioning, forced-air heating, and numerous thoughtful upgrades that make this home both economical and exceptionally easy to maintain. Whether you're searching for a full-time residence, seasonal retreat, or unique Florida getaway, this distinctive home offers an unmatched blend of tropical charm, sustainable living, and outdoor enjoyment that's rarely found in Naples.



$310,000
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Trail Acres

125 4th St, Naples, FL 34113

Homes - 864 ft² / 2,204 ft² - 2 Car Garage

2 Bed / 1 Baths

Built 1979
Trail Acres Naples Homes for Sale: INVESTOR ALERT! This 2-bedroom, 1-bath home is being offered as-is with the right to inspect. Featuring tile flooring throughout, this property offers low-maintenance living and great investment potential. The spacious two-car garage provides ample room for parking, storage, or a workshop while keeping your vehicles protected from debris. Whether you're looking to add to your investment portfolio or renovate and resell, this property presents an excellent opportunity. Please see confidential remarks for additional information.



$636,000
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Trail Acres

183 7th St, Naples, FL 34113

Homes - 1,790 ft² / 2,190 ft² - 2 Car Garage

3 Bed / 2 Baths

Built 2000
Trail Acres Naples Homes Under Contract: Welcome to this beautifully renovated residence offering the perfect blend of modern comfort and South Naples convenience. This meticulously updated home delivers both functionality and refined style. The interior showcases a bright and open layout enhanced by quality finishes and meticulous attention to detail throughout, ideal for both relaxing and entertaining. The home features 3 generous bedrooms with ample closet space, 2 full baths, and 1,790 sq. ft. of air-conditioned living space. The renovated kitchen stands out with stainless steel appliances, white cabinetry, and light-patterned tile flooring that flows into a breakfast nook and throughout the home for a cohesive and modern look. The primary suite delivers comfort and style with a large bedroom and a stunning bathroom that includes a dual vanity and an oversized walk-in shower. A 2-car garage provides you with plenty of space for all of your toys and/or tools. The roof was replaced in 2018 and the A/C unit is three-years-old; offering peace of mind and efficiency for years to come. The property was recently painted inside and out, creating a clean and welcoming feel from the moment you arrive. The entire property is fully fenced and features a remote-controlled entry gate, creating a private and secure setting. The screened lanai extends the living area outdoors; perfect for hosting year round. The backyard has been meticulously maintained and offers generous space for outdoor entertaining, gatherings, or future customization. Ideally located, this home offers easy access to the best of Naples living. The home is just a short drive to downtown Naples, area beaches, parks, dining, shopping, and everyday conveniences. It is also within convenient proximity to Lely Resort, known for its championship golf courses, resort-style amenities, and beautifully maintained surroundings. This is truly an exceptional opportunity to own a move-in-ready home in a desirable South Naples location.



$398,500
Sold Price:
$390,000
Sold Date:
03/24/2026
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Trail Acres

111 7th St, Naples, FL 34113

Homes - 1,175 ft² / 1,249 ft² - 1 Carport

3 Bed / 2 Baths

Built 1982
Trail Acres Naples Homes: Seller is offering Buyer a $5,000 Concession towards Closing Costs! Great value opportunity in Naples. This 3-bedroom, 2-bath single-family home is located just seven miles from downtown Naples and the Gulf’s white sand beaches, offering strong potential for investors or buyers seeking flexibility with no HOA fees or rental restrictions. Set in a quiet residential neighborhood minutes from Celebration Park, Naples Bay, Tin City, shopping, dining, and county parks, the location supports both long-term and seasonal demand. Several key improvements have already been completed, including a new roof (2022), a new electrical panel, a new water heater, and an updated kitchen with newer cabinetry and countertops. The home has also been freshly painted inside and out. The layout includes a comfortable living and dining area, a primary bedroom with a private bath, and two additional bedrooms that work well for guests or a home office. Laundry is located inside the home. The large fenced backyard offers room for future improvements such as an outdoor living space or a pool, providing additional upside. An attached carport offers covered parking, and a separate storage area adds functionality. Whether held as a rental or improved over time, this property represents a solid entry point into the Naples market with location, updates, and opportunity at an attractive price.



$379,000
Sold Price:
$370,000
Sold Date:
03/31/2026
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Trail Acres

277 Benson St, Naples, FL 34113

Homes - 1,048 ft² / 1,240 ft² - 1 Car Garage

3 Bed / 2 Baths

Built 1995
Trail Acres Naples Homes: Great investment opportunity!!! This residence boasts a spacious lot, cathedral ceiling and new vinyl bedroom floors. The home features new ceiling fans in guest bedrooms.The spacious, screened lanai is perfect for entertaining and floods the home with natural light through the glass sliding doors. New Roof installed in 2020. This home also has a laundry room and an attached one-car garage.It is conveniently located near the white sand beach of Marco Island and downtown Naples. The home is elevated enough to obtain a very reasonable flood insurance plolicy.



$325,000
Sold Price:
$285,000
Sold Date:
05/28/2026
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Trail Acres

156 4th St, Naples, FL 34113

Homes - 768 ft² / 976 ft²

2+Den / 1 Baths

Built 1969
Trail Acres Naples Homes: An exceptional opportunity in one of Naples’ most sought-after locations, 156 4th Street presents a compelling canvas for first-time home buyers, investors, renovators, or anyone seeking value, flexibility, and long-term upside. This 2-bedroom residence with a versatile den and 1 bathroom is being offered AS-IS, providing a rare chance to reimagine or enhance a property in an established Naples neighborhood with strong rental, resale demand, NO HOA and low taxes. The functional layout allows for multiple configurations, whether maximizing rental income, creating a seasonal retreat, or planning a thoughtful renovation to elevate future returns. A key advantage of this property is the assumable flood insurance policy, offering added convenience and potential cost savings for the next owner. The home has a history of rental use, and previous rental income information is available upon request, making this an attractive option for buyers focused on cash flow, short-term rental potential, or long-term appreciation. Ideally positioned near Naples’ renowned dining, shopping, beaches, and lifestyle amenities, 156 4th Street combines location, opportunity, and investment appeal—an increasingly rare find in today’s Naples real estate market. Whether you’re seeking your next income-producing property or a value-driven project in a prime coastal setting, this offering delivers exceptional potential.



$240,000
Sold Price:
$247,000
Sold Date:
07/31/2026
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Trail Acres

133 2nd St, Naples, FL 34113

Homes - 916 ft² / 1,324 ft²

3 Bed / 1 Baths

Built 1970
Trail Acres Naples Homes: Opportunity awaits in the heart of Naples! This handyman special offers incredible potential for investors, contractors, flippers, or buyers looking to create their own vision. Situated on a desirable lot just minutes from downtown Naples, world-famous beaches, shopping, dining, and entertainment, this property presents a rare chance to renovate, rebuild, or reimagine in a highly sought-after location. The home is being sold as-is and is priced to reflect its condition. Whether you're looking for your next investment project or a property to customize from the ground up, this is your opportunity to add value in one of Southwest Florida's most desirable markets. Conveniently located near major roadways, schools, parks, and all that Naples has to offer. Bring your contractor and your imagination—properties with this level of potential and location are becoming increasingly difficult to find.




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Need professional assistance selling your property at Trail Acres Naples? Find out how an Area Specialist can help to generate more property exposure in order to get the most money for your investment in the least amount of time.Contact Us.
*Just Listed: new properties that came on the market within the last 5 days.
*Decrease/Increase: listing values that are being recorded within the last 30 days.
*Foreclosures/Short Sale: Please note, all properties are subject to bank approval. Buyers must be pre-approved or show proof of funds before submitting an offer.

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