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Homes for Sale with a Pool in 34108, Naples, FL

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Welcome to your dedicated resource for homes for sale with a pool in 34108, Naples, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local 34108, Naples, FL agents, The Fortune Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the with a pool properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Homes for Sale with a Pool in 34108, Naples, FL

$10,250,000
4 Beds ⋅ 4.5 Baths ⋅ 226002482 MLS ⋅ Windsor At Bay Colony BLDG.
On the pristine beach of the prestigious, private and gated enclave of Bay Colony, The Windsor epitomizes luxury coastal living. Upon arrival, the private elevator opens to reveal breathtaking uninterrupted panoramic views. The residence boasts an impressive 6,085 square feet of thoughtfully designed living space, complemented by three generous lanais inviting you to savor spectacular sunrises and sunsets every day of the year. The meticulously crafted floor plan features elegant marble flooring, a luxurious primary suite with spa-like bath, three guest bedrooms all with en suites, a versatile office with bonus Gulf view, and a chef's kitchen that seamlessly flows into the inviting family room and breakfast nook. The decor and style have been expertly created to be soothing and warm. The Windsor has undergone a complete transformation offering unparalleled amenities designed to elevate every aspect of your lifestyle. These include 24-hour staffed concierge desk, a well-appointed conference room and elegant social lounge, a resort-style pool, a state-of-the-art fitness center and three charming guest villas for your visitors.

8477 Bay Colony DR Unit 902, Naples
$3,900,000
4 Beds ⋅ 4.5 Baths ⋅ 225076143 MLS
This magnificent Gulf access waterfront home has been renovated and updated to like new status - kitchen, metal roof, bathrooms, flooring, pool and spa resurfacing, paint inside and out, garage doors, landscaping and lighting - all done! Almost 3700 sq. ft. under air, with the owner's suite on the first floor, a bedroom with ensuite bath and balcony on the second level, and two more bedrooms with a balcony on the third level and a breakfast bar, giving everyone their private space. Entering the foyer, you will be impressed by the sense of openness and luxury, the high tray ceilings, and views to the huge lanai, pool, and your dock beyond on the wide canal. Like new chef's kitchen with gas cooktop, custom cabinets, stainless KitchenAid appliances, and beautiful Pompeii Quartz countertops throughout the home. The owners suite, living area, family room and den/office all have water views, and the corner sliders open up for indoor/outdoor living. A 13000 pound lift with a new cover is ready for your boat, and the dock also has a jet ski lift and underwater lighting. Full hurricane protection with impact windows and electric roll down shutters. This home has been lightly used and perfectly maintained by the owner. Minutes to the Mercato and beaches, convenient to downtown Olde Naples. Less than 2 miles by boat to Wiggins Pass and the open ocean. Come see this home and you will fall in love.

447 Egret AVE, Naples
$1,749,000
3 Beds ⋅ 2 Baths ⋅ 226001380 MLS ⋅ La Scala At Vanderbilt Beach BLDG.
Majestic views of the Bay & Gulf from this updated Vanderbilt Beach condo that comes with a DEEDED BOAT SLIP WITH 24,000. This unit boasts never-ending trade winds year-round! Delight in front row seats to unobstructed sunrises from the spacious screen lanai that runs the length of your home & sunsets from right outside your front door. The upgraded master ensuite bath boasts double vanities, rich wood cabinetry & a high-end walk-in shower with various jets promising the most luxurious bathing experience. Kitchen is outfitted with stainless-steel appliances, Bay views, eat-in breakfast bar & adjacent dining area. This condo is decked out in an eye-pleasing neutral motif that allows you to cosmetically update/decorate to your exact taste & style. La Scala is a low-density condo building steps from Vanderbilt Beach. Amenities include beach access steps from your front door, boat docs with water & electricity, a community pool & more. Unbeatable location, steps from the Gulf of Mexico & within walking distance to fine dining at La Playa & the Turtle Club. Enjoy paradise with this perfect vacation getaway or forever home. All hurricane assessments have been paid.

9700 Gulf Shore DR Unit 202, Naples
$2,225,000
4 Beds ⋅ 3 Baths ⋅ 226001094 MLS
A rare investment opportunity and the only multifamily-style residence currently available in the entire Connors area of Vanderbilt Beach. This exceptional Gulf-access waterfront property offers versatility, usability, and long-term value, set on an oversized corner lot with approximately 105 feet of canal frontage. Constructed of concrete block and designed as a single-story residence, the property features a primary home plus a separate guest apartment, creating a flexible layout ideal for personal use, income potential, or extended family living. A private dock is already in place and accommodates two boat lifts, including one lift with a boathouse, providing protected and convenient boating access. The wide canal offers open water views, excellent maneuverability, and a desirable setting within one of Naples’ most established boating communities. Outdoor living is a standout feature of the property, thoughtfully designed for both entertaining and relaxation. Enjoy the beautiful infinity-edge pool surrounded by an expansive paver deck, along with a canal-front tiki hut featuring a full bar, Bluetooth speaker system, and scenic water views—perfect for sunset gatherings. A pergola with integrated lighting creates an inviting space for evening dining or lounging, while a private 7-hole mini-golf course adds a distinctive and rarely found amenity that enhances both lifestyle enjoyment and guest appeal. Interior spaces are comfortable, stylish, and fully updated, featuring a split-bedroom floor plan, abundant natural light, and seamless indoor-outdoor connectivity. The entire interior has been completely renovated with modern finishes and improved functionality throughout. The single-level design enhances accessibility and everyday livability. The main residence includes three bedrooms plus a den and two full baths. A separately metered guest apartment with private entrance and dedicated parking offers one bedroom, one bath, kitchen, living area, laundry, and screened porch—allowing for independent use or rental flexibility. Recent improvements include a new roof, impact-resistant windows and sliders throughout, and storm surge protection, providing added peace of mind and long-term durability. With multiple living spaces, two boat lifts, and direct Gulf access, this canal-front property offers a level of flexibility rarely found in the Connors area and supports a wide range of ownership strategies. Ideally located near Vanderbilt Beach, the Ritz-Carlton, and Mercato, with convenient access to premier dining, shopping, and coastal amenities, this property presents a compelling opportunity in one of Naples’ most desirable waterfront neighborhoods.

493 Willet AVE, Naples
$4,900,000
5 Beds ⋅ 6 Baths ⋅ 226000197 MLS
One or more photo(s) has been virtually staged, AI generated or rendered. An extraordinary opportunity to complete this exceptional waterfront estate on the widest canal in Vanderbilt Conners! Just moments from the sugar-sand beaches of Vanderbilt. Positioned on a lot with exceptionally wide water views. Custom home boast over 5,700 square foot and is constructed on pilings offering discerning buyers the rare opportunity to fully customize a modern coastal masterpiece to their exact vision. The home is thoughtfully designed for grand waterfront living, featuring an infinity-edge pool, fire pit, privacy wall, and newly constructed seawall, all oriented to maximize sweeping water views and breathtaking sunsets. The expansive footprint allows for six or more cars in tandem, ideal for all the toys and car enthusiast! Set along one of the most impressive waterways in Conners, the property enjoys sparkling water views and Gulf-access boating creating a dramatic backdrop for elevated indoor and outdoor living. With windows, doors, and interior finishes yet to be selected, this residence invites the future owner to curate every detail, from luxury materials and bespoke millwork to a chef’s kitchen, spa-like primary suite, and refined entertaining spaces. Enjoy the ultimate in boating from your own backyard! Surrounded by estate homes and offers both privacy and prestige. Just minutes to Vanderbilt Beach, the Ritz-Carlton, LaPlaya, Mercato, and Naples’ finest dining and shopping, this is an opportunity to save years of planning and permitting while still creating a fully custom personalized luxury waterfront retreat. A truly exceptional offering where vision meets location, scale, and lifestyle—on one of Naples’ most coveted and widest waterways.

415 Seabee AVE, Naples
$749,999
3 Beds ⋅ 2 Baths ⋅ 226001663 MLS
Set on a highly desirable corner lot in the highly desired 500 block of Naples Park, this coastal property presents an exceptional opportunity to own in one of Naples’ most sought-after neighborhoods. Elevated approximately 14 feet above sea level and located outside the flood zone, the home has remained free of hurricane damage, offering a rare combination of peace of mind and premier location. Surrounded by a community experiencing ongoing luxury redevelopment, the property is ideal for those seeking a move-in option with future potential or a canvas for customization. A metal roof installed in 2015 adds long-term value and durability, while the professionally landscaped grounds and paver patio create a private outdoor retreat enhanced by an automatic aquifer-fed irrigation system. Just one block west, enjoy direct access to Vanderbilt Lagoon and the turquoise waters of the Gulf of Mexico. Vanderbilt Beach’s white sand shoreline is moments away, perfect for sun-soaked afternoons, waterfront dining, and unforgettable sunset strolls. Naples Park residents benefit from eligibility for a complimentary annual beach parking pass, extending easy access to beaches throughout Naples and Collier County. Ideally located near Mercato’s upscale shopping, dining, nightlife, and entertainment, as well as Whole Foods, Trader Joe’s, Publix, and everyday conveniences, this property offers an unparalleled coastal lifestyle. With strong neighborhood pride and increasing demand for this location, the home represents a compelling opportunity to secure a foothold in one of Naples’ most vibrant coastal communities.

595 103rd AVE N, Naples
$677,000
2 Beds ⋅ 2 Baths ⋅ 226001594 MLS ⋅ Interlachen BLDG.
Experience the ultimate Pelican Bay lifestyle in this beautifully updated, turnkey furnished 2 bedroom, 2 bath residence in the sought-after Interlachen community. Overlooking a tranquil pond and water feature, this light-filled home offers an exceptional blend of luxury, comfort, and convenience. The open concept floor plan is enhanced by elegant marble tile, brand new luxury vinyl flooring, fresh interior paint, and a spacious kitchen featuring stainless steel appliances, a pantry, and a newly added breakfast bar designed for effortless entertaining. The inviting glass-enclosed and screened sunroom creates the perfect year-round retreat, offering peaceful water views and seamless indoor-outdoor living. Interlachen residents enjoy a private island style pool and spa surrounded by lakes, fountains, and lush tropical landscaping. A new roof was installed in 2024, and for added value and peace of mind, there is a one-year home warranty included. Located just steps from the Pelican Bay tram system, residents enjoy easy access to nearly three miles of pristine white sand beaches, scenic boardwalks through protected mangroves, private beachfront dining, world-class tennis facilities, a state-of-the-art fitness center, walking and biking paths, and an unmatched resort-style lifestyle. Pelican Bay remains Naples premier beachfront community, offering a rare combination of luxury, nature, wellness, and coastal living. Whether you're seeking a seasonal retreat, full-time residence, or lock-and-leave Naples getaway, this exceptional condo delivers the very best of Southwest Florida living.

6760 Pelican Bay BLVD Unit 312, Naples
$950,000
4 Beds ⋅ 2.5 Baths ⋅ 225085040 MLS
Motivated Seller! Stunning 4 bedroom 2 1/2 bath home in Naples Park less then mile to Vanderbilt Beach. Completely renovated in 2022, plumbing, electric, a/c, walls, metal roof, this property is amazing. Upgraded recessed LED lights in all rooms. Custom doors complement each room. Hugh chefs kitchen with 42" cabinets with deep drawers. Quartz counter top paired with beautiful backsplash and high end appliances. French doors to the covered patio with large picture window screen. Primary bedroom has sliders to the pool and a beautiful primary bathroom. Large screened in pool deck great for entertaining. Fenced backyard with PVC fencing. Low carry cost with no HOA, GREAT RENTAL INCOME property. Located minutes to so many popular Naples hot spots such as Vanderbilt Beach, Ritz-Carlton, Mercado shops and fine dinning restaurants. Home comes with/ one year home warranty for buyer comfort.

648 100th AVE N, Naples
$524,900
3 Beds ⋅ 2 Baths ⋅ 225084138 MLS ⋅ Beachwalk Gardens BLDG.
North Naples beach living and investment potential come together in this 3-bedroom, 2-bath condo in Beachwalk, a gated community less than a half mile from Vanderbilt Beach in Naples, Florida. A resident gate near the building connects directly to the sidewalk along Vanderbilt Beach Road, so you can walk or bike to the Gulf of Mexico in minutes instead of dealing with beach parking and traffic. Morning walks, midday breaks at the shoreline, and sunset visits can be part of your daily routine. The 3/2 layout supports a range of uses: full-time residence, seasonal home, or income-producing property. Beachwalk is a popular choice for seasonal renters, giving owners an attractive opportunity for short- or longer-term rental income, subject to association rules. The lock-and-leave convenience and proximity to the beach make this condo especially appealing for buyers focused on both personal use and cash-flow potential. Residents enjoy two heated pools, spa, six tennis courts, bocce, fitness room, clubhouse, and a 24-hour manned gate, all within a walkable North Naples setting. From your front door, you are close to Mercato and Pavilion and within easy reach of restaurants, cafés, Publix, CVS, the library, movie theaters, and a nearby walk-in clinic. For buyers who want a condo near Vanderbilt Beach with strong rental demand, everyday convenience, and resort-style amenities in one of Naples? most desirable coastal corridors, this Beachwalk residence is a compelling option.

592 Beachwalk CIR Unit N102, Naples
$279,000
1 Baths ⋅ 225085065 MLS ⋅ Vanderbilt Towers BLDG.
Experience spectacular sunsets and hear waves crash on the beach from this turnkey and completely remodeled Sea-Efficiency! Just steps to the beach with western exposure and tranquil views over the Wiggins State Park mangrove preserve. Privacy and peace of mind are provided by both impact sliders AND electric lanai shutters. Have it all with with tile flooring, granite countertops, stainless steel appliances and new cabinets throughout. Nothing to do but relax and enjoy your upgraded Hi Hat lighting with lovely contemporary furnishings including a Murphy Bed, Flat Screen TV and Leather Sofa. HUGE storage unit down the hall. Great investment as this condo can be rented 12 times per year for a minimum of 30 days. Vanderbilt Towers II has an in house manager plus marina and boats slips that can be rented when available. Daily walks to Vanderbilt Beach, the Turtle Club and La Playa with fine dining and shopping at Mercato just a few minutes drive away! Discover "Paradise on a Dime" on the quiet yet convenient Bluebill peninsula.

3 Bluebill AVE Unit 405, Naples
$1,295,000
2 Beds ⋅ 2 Baths ⋅ 225083539 MLS ⋅ St Pierre BLDG.
A Truly “Special Location” in Pelican Bay……This St. Pierre 10th floor residence (2 Bedrooms / 2 Baths + Office Area)... offers you those Special “Sun Sets”, and great “views” to the Gulf of America ! This home has recently been remodeled and upgraded….its as good as “new” ! Some of the upgrades: New Air Conditioning system, Wood flooring, interior repainted, open kitchen remodeled with “stone counter tops”, “marble backsplash”, new appliances. Both bathrooms were remodeled with “walk in” showers, a “free standing” tub, stone counter tops, and new fixtures. This residence comes with "2" PARKING SPACES - one is an assigned covered parking space - on the 2nd floor of the parking garage - plus one other exterior parking space. The St. Pierre building is located within a "gated community / has “3” guest suites that are available for residents to reserve / a “fitness center” totally remodeled w/ new exercise equipment. / onsite “Tennis Courts”, “Pickle Ball Courts” / "Bocce Ball Courts", and a "heated pool & spa". The St. Pierre building has recently completed a total remodeling of its interior Amenities and Common Areas, plus total refurbishing of the landscaping, and repainting of the building. The St. Pierre’s location is “5 star” - a short walk to the “Tram Station" which provides shuttle rides to the beach” Pelican Bay's amenities / community center w/ fully staffed fitness/life center / trainers, classes / tennis and pickle ball center. Pelican Bay has “2” beachfront restaurants / both casual & formal dining …open only to Pelican Bay residents / accessible by golf style “tram”, bike or walking.....beach chairs/umbrellas, canoes, kayaks and sailboats available. There are over 15 miles of walking, jogging and bike trails located within Pelican Bay, as well as the option to join the private Pelican Bay Golf Country club. Pelican Bay Community itself has the perfect Naples location / just minutes away from the Artis-Naples (formerly the Naples Philharmonic), the upscale Waterside Shops, Mercato’s shops and restaurants, and the charming 5th ave and 3rd street shops featuring their “many” fine dining restaurants. This condo residence location, being in the St. Pierre building, is one of the few that offers (a) the “ease of beach access”, and (b) being fullly remodeled making it “move in ready” ! Don’t miss “looking” at this residence - you will “Fall in Love with it” !

6825 Grenadier BLVD Unit 1002, Naples
$850,000
4 Beds ⋅ 2 Baths ⋅ 225083353 MLS
Discover a versatile Naples Park income property designed for both lifestyle and returns—just a short stroll to Mercato, Patio Café, and the shops/restaurants along US-41. This fully fenced property (owner-owned fencing surrounding the entire lot) offers two separate living spaces with generous parking via large driveways serving both units—perfect for tenants, guests, or multi-generational living. The 1-bedroom/1-bath unit is currently rented at $1,500/month on a month-to-month lease—providing immediate income with flexibility for a new owner to take over at any time. The showstopper is the fully remodeled 2-bedroom/2 - bath residence, featuring lake views and access to a private pool. This side has never been rented since the remodel—it was completed for the owner’s personal use, with quality finishes and thoughtful upgrades throughout. Ideal setup to live in the remodeled poolside unit and rent the other, or rent both to maximize cash flow. Also offers the potential to structure one unit for longer-term occupancy and the other for shorter stays (buyer to verify any rental rules/ordinances).

829 107th AVE N, Naples
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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.