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559/563 105th AVE N, Naples
$1,549,000
7 Beds ⋅ 4 Baths ⋅ 226037165 MLS
A polished set of Naples Park Duplexes positioned exactly 1.0 mile from the beach, offering strong rental appeal, exceptional lifestyle access, and the kind of beachside investment fundamentals that remain difficult to replicate. This well-maintained property features a total of 7 bedrooms and 4 bathrooms across 4x separate residences, making it an ideal short-term rental asset, seasonal retreat, or income-producing addition to a Naples portfolio. This offering creates a rare double-lot opportunity with scale, flexibility, and enhanced long-term value. The property is thoughtfully arranged around a large courtyard and includes ample parking, brand-new fencing, and a private pool completed in 2022, giving guests and owners a true resort-style outdoor setting. Its proximity to Vanderbilt Beach, Mercato, the Ritz-Carlton, Waterside Shops, and North Naples’ top restaurants makes it highly marketable for Airbnb and vacation rental demand. For investors seeking an excellent cap rate, beachside scarcity, and a low-maintenance asset in one of Naples’ most coveted rental corridors, this quadplex is a standout opportunity.

559/563 105th AVE N, Naples

683 100th AVE N, Naples
$1,999,999
7 Beds ⋅ 226036391 MLS
RENOVATED NAPLES PARK FOURPLEX ON A RARE DOUBLE LOT—OFFERED FURNISHED. Just minutes from Vanderbilt Beach, this exceptional residential-income property combines four beautifully updated residences, a private resort-style pool and spa, and an irreplaceable Naples Park location near the Ritz-Carlton, LaPlaya Beach & Golf Resort, Delnor-Wiggins Pass State Park, Mercato, Waterside Shops, Whole Foods, dining, and entertainment. Completed in 2023, the extensive renovation includes a new roof, hurricane-impact windows and doors, and a stunning new pool and spa. Two separate buildings encompass four furnished residences with a combined 7 bedrooms and 7 baths, thoughtfully arranged around a private central courtyard. The result is a rare property that offers both the flexibility of a multi-family investment and the appeal of a private coastal compound. The centerpiece is the beautifully designed outdoor living space: a sparkling pool and spa, expansive paver deck, outdoor shower, and multiple areas to gather, dine, relax, and enjoy the Naples sunshine. Whether spending the day at the beach, lounging by the pool, or entertaining beneath the palms, the setting delivers the indoor-outdoor lifestyle buyers want in Naples. Set on approximately 13,504 square feet across Lots 5 and 6, this oversized double-lot property offers privacy, space, and versatility that are increasingly difficult to find in Naples Park. Seven open parking spaces add convenience for residents and guests. Offered furnished, this is a ready-to-enjoy opportunity for an investor, a buyer seeking a multi-generational retreat, or anyone wanting a distinctive property close to the beach. More than a fourplex, this is a fully renovated Naples's lifestyle property where location, land, resort-style outdoor living, and income-producing potential come together.

683 100th AVE N, Naples

668 97th AVE N, Naples
$1,550,000
8 Beds ⋅ 4 Baths ⋅ 226032245 MLS
An Exceptional Coastal Investment & Lifestyle Opportunity Perfectly positioned in one of Naples’ most coveted walkable locations. This impeccably renovated dual-duplex property offers effortless access to Vanderbilt Beach and the vibrant Mercato district for world-class shopping, dining, and entertainment. Opportunities like this are rare—and this one delivers, generating over $185,000 in income in 2025. The property features two beautifully updated duplex buildings, totaling four spacious 2-bedroom, 1-bath residences. Each residence is thoughtfully designed for comfort and privacy, offering a private screened lanai with washer and dryer, and patio with BBQ grill, creating an ideal blend of indoor and outdoor living. At the heart of the property lies a lush, fully fenced backyard retreat, ideal for entertaining or relaxing under the Naples sun. Highlights include a covered pergola, fire pit, and generous space to add a custom pool, transforming the grounds into a true resort-style oasis. Ample parking accommodates up to 10 vehicles, a rare convenience in this premier location. A charming, gated courtyard entry, enhanced with security cameras, provides both elegance and peace of mind. Whether envisioned as a luxury income-producing asset, boutique vacation rental, or personal coastal compound, this remarkable property offers the perfect balance of sophistication, location, and lifestyle.

668 97th AVE N, Naples

2708-2714 Santa Cruz BLVD, Naples
$2,500,000
8 Beds ⋅ 8 Baths ⋅ 2026035039 MLS
Rare Kings Lake offering combining immediate rental income with documented additional development potential. Seven-parcel, 1.54± acre assemblage: a fully occupied four-unit townhome building (four separately deeded fee-simple residences under one roof), a separately deeded common-area parcel with private heated saltwater pool, and two adjoining vacant development parcels. Listing includes PID #'s - 52951440000, 52951200004, 52951160005, 52951240006, 52951280008, 52951320007, 52951360009. The four residences — 8 BR / 8 BA plus 2 dens, 4,432± SF combined— feature private detached garages, secluded patios, second-level lanais on the inside units, impact-rated windows, and beautifully landscaped, lake-oriented grounds. 100% occupied on annual leases with $120,240 in annualized scheduled rent and strong tenant history. Seller has obtained a Collier County Zoning Verification Letter documenting the property’s development history and the potential for additional multifamily development on the two vacant parcels, subject to applicable requirements and county approvals. Professional boundary survey, engineering documents, concept plans, and the Zoning Verification Letter are available, with additional operating information provided to qualified purchasers. Minutes to Fifth Avenue South, downtown Naples, and Gulf beaches. List price reflects the entire seven-parcel portfolio. Components also available separately: vacant west parcel (MLS #2026041176, east parcel by offer) and the fourplex (separate listing). Well suited to investors, developers, builders, family offices, and 1031 exchange buyers. All information deemed reliable but not guaranteed; buyers to verify.

2708-2714 Santa Cruz BLVD, Naples

3365 Estey AVE, Naples
$1,049,900
4 Beds ⋅ 226026942 MLS
UPDATED FULLY OCCUPIED FOUR-UNIT INVESTMENT OPPORTUNITY – NEVER FLOODED! Rare opportunity to own two adjacent duplexes totaling four 1-bedroom, 1-bath residences in a highly desirable central Naples location. Offering proven rental history, private on-site parking, and strong income potential, this property is well suited for investors seeking immediate cash flow with long-term appreciation. Several units have been thoughtfully updated with herringbone-pattern tile flooring, quartz countertops, modern cabinetry, stainless steel appliances, renovated bathrooms, new windows, energy-efficient mini-split A/C systems, and on-demand water heaters. Select units also feature private screened lanais, adding desirable outdoor living space for tenants. The buildings have been well maintained, with roofs replaced in 2006 and reported to be in good condition. Additional opportunities remain to further enhance rental income and overall value. Ideally located just minutes from Downtown Naples, Fifth Avenue South, Naples' world-famous beaches, Celebration Park, Publix, shopping, dining, pickleball courts, and major conveniences, the property benefits from consistent tenant demand in one of Southwest Florida's most sought-after rental markets. Whether you're expanding your investment portfolio, completing a 1031 exchange, or seeking a well-located multi-family asset with immediate income and future upside, this is a rare opportunity in the heart of Naples.

3365 Estey AVE, Naples

2316 Bayside ST, Naples
$849,900
8 Beds ⋅ 4 Baths ⋅ 226017096 MLS
Fully Remodeled Quadplex in the Heart of Naples – 2316 Bayside St; Welcome to 2316 Bayside Street, a completely remodeled quadplex offering exceptional investment potential in one of Naples’ most desirable and rapidly growing areas. Situated just minutes from world-renowned beaches, 5th Avenue shopping and dining, and top-rated schools, this property combines modern upgrades with an unbeatable location. Each of the four units has been fully renovated with high-quality finishes, including new kitchens with quartz countertops and stainless steel appliances, updated bathrooms, luxury vinyl plank flooring, and contemporary lighting and fixtures throughout. The property features impact-resistant windows, a new roof, updated electrical and plumbing systems, and central HVAC—ensuring low maintenance and long-term value. Whether you're an investor looking for strong rental income or a buyer seeking multi-generational living options, this quadplex checks all the boxes. With Naples’ rental demand continuing to surge, 2316 Bayside St represents a rare opportunity to own a turnkey income-producing property in the heart of paradise. Don’t miss your chance to secure this exceptional asset in one of Florida’s most sought-after coastal markets.

2316 Bayside ST, Naples

280 Indies DR E Unit 101,102,201,202, Naples
$1,800,000
12 Beds ⋅ 8 Baths ⋅ 225069501 MLS
Seller Paid Maintenance Fees for 2 years. Rare new construction assemblage offering at Bonnaire in Antilles Naples Area‚ four Classic Coach Home condominium residences in Building #26 (Units 101, 102, 201, and 202) conveyed together as a full condminium building package. The developer will pay two years condominium fees, with a minium of 4 units purchased. This advantage reduces ownership costs, strengthens ROI investment performance and enhances buyer value from day one. This assemblage totals 12 bedrooms, 8 baths, 4 kitchens and 4 garages. The lower Saba plans (101 and 102) each feature 1,537 sq. ft. of open living with 3 bedrooms, 2 baths, breakfast-bar kitchens, walk in closets, screened lanais, and attached garages, (2010SF TTL). The upper Tobago plans (201 and 202) provide 1,509 sq. ft. with 3 bedrooms, 2 baths, soaring ceilings, private entries, walk-in closets, screened lanais, and garages (1988SF TTL). Both floor plans showcase the elevated finishes that define 2025 resort-style living in Southwest Florida, including 10' volume ceilings, solid wood cabinetry and doors, Kohler fixtures, stainless steel appliances, Quartz countertops, frameless glass showers, in-unit laundry room,12''x 24'' porcelain tile flooring, wide profile baseboards, impact-rated windows and doors, and solid CBS construction. Antilles is a West Indies-inspired community just north of Fiddler's Creek, set on 54 acres with 5 acres of lakes and preserves, anchored by the Flamingo Club -a 5,000 sq. ft. clubhouse with infinity-edge pool and spa, fitness center, social lounges, catering kitchen, and conference space, along with bocce and pickleball courts, putting green, tiki bar, fire pit lounge, and walking trails. Pet and golf cart friendly. Leasing allowed for 30 days, 3x per year, up to 365 days. Monthly HOA, maintenance fee, and 1x capital contribution per unit apply. No flood insurance required. Perfectly situated between Marco Island and Downtown Naples Area - renowned for their pristine beaches, marinas, world-class dining, and vibrant resort lifestyle - this rare full-building assemblage offers strong income potential for seasonal or annual rental, while securing a new premier luxury asset in Southwest Florida. Building 27 is concurrently for sale and can be purchased individually or alongside Building 26 for a complete assemblage. Please enquire.

280 Indies DR E Unit 101,102,201,202, Naples

The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.