Olde Naples Homes with Pool

Olde Naples Homes with Pool

Welcome to Olde Naples, a charming and historic subdivision nestled in the heart of Naples, Florida. This enchanting neighborhood is renowned for its stunning architecture, lush landscapes, and vibrant community atmosphere. Characterized by its picturesque streets lined with swaying palm trees and beautiful homes, Olde Naples truly embodies the essence of coastal living.

As you explore this delightful area, you'll discover an array of exquisite homes, many of which feature private pools that invite you to indulge in the ultimate Florida lifestyle. Imagine relaxing by your own sparkling oasis, surrounded by tropical foliage, while enjoying the warm sunshine that Naples is famous for. Whether you’re hosting summer barbecues or simply unwinding after a long day, a poolside retreat in Olde Naples offers the perfect backdrop for creating cherished memories.

The charm of Olde Naples extends beyond its stunning residences. Residents enjoy easy access to pristine beaches, upscale shopping, and gourmet dining options, all just a stone's throw away. The vibrant community is also home to art galleries, cultural events, and lively farmers' markets, fostering a sense of connection and camaraderie among neighbors.

With its blend of luxury, leisure, and convenience, Olde Naples is more than just a place to live; it’s a lifestyle. If you’re seeking a serene escape with the added benefit of a private pool, this subdivision promises a unique opportunity to experience the best of Florida living. Come and discover your dream home in Olde Naples, where every day feels like a vacation!

Newest Olde Naples Homes with Pool

4 Beds ⋅ 6 Baths ⋅ Olde Naples SubDv.

TWO EXCEPTIONAL OPPORTUNITIES. ONE EXTRAORDINARY ADDRESS. Perfectly positioned in the heart of Old Naples, this beautifully reimagined residence offers a rare opportunity to embrace today's luxury lifestyle while investing in tomorrow's possibilities. Just moments from the Gulf beaches, Fifth Avenue South, Third Street South, and the exciting transformation reshaping Downtown Naples, this exceptional property appeals to two distinct buyers: those seeking a sophisticated, move-in-ready luxury home and those who recognize the extraordinary long-term value of one of Old Naples' premier homesites. Thoughtfully reconstructed and beautifully updated, the home blends timeless coastal elegance with comfortable everyday living. Expansive open-concept gathering spaces flow effortlessly from the gourmet kitchen to the indoor and outdoor living areas, creating the perfect setting for everything from intimate family dinners to large-scale entertaining. A private upstairs guest retreat offers exceptional flexibility for extended family, visiting guests, or a secluded home office, while every space has been designed with both comfort and functionality in mind. Equally impressive is the outdoor setting. Unlike many Old Naples properties where the home occupies nearly the entire lot, this residence offers a southern-exposure backyard with room to truly enjoy the Florida lifestyle. Relax beside the pool and spa, envision a custom outdoor kitchen, entertain beneath the stars, or simply enjoy the rare open green space for children, grandchildren, or pets to play. Beyond the property itself lies one of its most compelling attributes; its location at the center of the next chapter of Old Naples. As remarkable new luxury developments, elevated hospitality experiences, world-class dining, boutique shopping, and exciting new destinations continue to redefine the downtown landscape, this already coveted neighborhood is becoming even more desirable. More than simply acquiring a beautiful home, you're investing in one of Old Naples' most coveted locations—offering the rare opportunity to enjoy TWO EXCEPTIONAL OPPORTUNITIES. ONE EXTRAORDINARY ADDRESS.

742 11th Avenue S, Naples

6 Beds ⋅ 7 Baths ⋅ Olde Naples SubDv.

This Gulf-front masterpiece offers an unparalleled blend of location, luxury, Gulf views, and resort-style living. Completely rebuilt in 2024 by Kukk Architecture and The Lykos Group with the exception of one exterior wall to utilized the grandfathered setbacks and maximize an oversized building envelope. The home has experienced no water intrusion in living areas during recent weather events. The residence combines historic charm with sophisticated elegance. Originally built in 1886, the home underwent an extensive three-year renovation and reconstruction. Now practically new, the residence preserves its heritage, grandfathered footprint, and distinctive character while offering modern luxury throughout. The 6,100-square-foot, fully air-conditioned living space maximizes its premier beachfront setting. The well-designed layout offers five spacious bedrooms, five full and two half baths, a private study, and a flexible sixth bedroom. Sweeping Gulf views provide a stunning backdrop. The gourmet kitchen boasts dual Cristallo quartzite islands, top-tier appliances, custom cabinetry, and a service kitchen. Additional features include a private gated entry, two fireplaces, elevator, whole-house generator, automated screens/shutters, water filtration, and ultra-efficient air conditioning. Perfectly positioned on the Gulf, just moments from the dining and boutique shopping of Third Street South and Fifth Avenue South. A rare opportunity in the heart of Old Naples.

55 13th Avenue S, Naples

3 Beds ⋅ 4 Baths ⋅ Olde Naples SubDv.

On a desired, tree-lined street in the heart of Old Naples, this exceptional residence offers refined coastal luxury just moments from the pristine Gulf beaches and the acclaimed dining, shopping and entertainment of Fifth Avenue South. Situated within The Gables on Sixth Street, an exclusive enclave of only seven residences designed by Harrell & Associates, the home combines privacy, sophistication and an unrivaled location. A gated rear entrance leads to an air-conditioned three-car garage complete with a vehicle lift and custom built-in storage. Spanning more than 4,300 square feet of beautifully designed living space, the light-filled interior showcases rich hardwood and stone flooring, elegant architectural details and a seamless open-concept floor plan. The redesigned chef’s kitchen serves as the heart of the home, featuring premium appliances, custom cabinetry, an oversized island ideal for entertaining and a climate-controlled wine room with capacity for more than 450 bottles. Designed to embrace the Naples lifestyle, expansive walls of glass connect the great room to a stunning outdoor living area. The covered lanai, highlighted by striking glass floor panels suspended above the pool and spa, creates a dramatic architectural focal point. A fully equipped summer kitchen, gas fireplace and retractable screens provide the perfect setting for year-round entertaining and relaxation. The second floor offers three generously sized en-suite guest bedrooms, while the luxurious primary suite serves as a private retreat complete with a serene balcony and spa-inspired bath featuring exceptional finishes and thoughtful design. Absolutely no water intrusion from past hurricanes. Blending timeless elegance, modern comfort and an extraordinary convenient location, this residence represents a rare opportunity to enjoy a luxurious coastal lifestyle and the best of Old Naples living.

32 6th Street S, Naples

4 Beds ⋅ 6 Baths ⋅ Olde Naples SubDv.

One or more photo(s) has been virtually staged, AI generated or rendered. Set just steps from the Gulf and the celebrated boutiques and restaurants of Third Street South and Fifth Avenue South, this extraordinary newly built estate embodies the pinnacle of refined Old Naples living. Crafted in 2017, this gorgeously furnished four-bedroom + den residence offers an exceptional blend of timeless coastal elegance and modern luxury across an impeccably curated floor plan. From the moment you enter, the home captivates with soaring ceilings, wide-plank French oak flooring, bespoke millwork and designer lighting that create an atmosphere of understated sophistication. Walls of glass fill the interior with natural light, while seamless indoor-outdoor transitions invite effortless entertaining and relaxed resort-style living. At the heart of the home, the spectacular chef’s kitchen is a true statement of luxury and design, featuring an oversized island, a commanding 48-inch Wolf gas range, dual Sub-Zero refrigeration, Miele built in wine refrigerator, Miele built-in coffee system, premium fixtures and custom cabinetry tailored for both grand-scale entertaining and everyday comfort. Adjacent living and dining spaces are anchored by a beautiful private tropical retreat where every detail has been thoughtfully considered. The outdoor Oasis features a stunning custom pool and spa with oversized sun shelf, towering private bamboo hedge, and outdoor kitchen, creating an atmosphere reminiscent of an exclusive luxury resort. The first-floor primary suite is a serene sanctuary, offering spa-like amenities, a luxurious bath retreat and a custom walk-in wardrobe. A private detached cabana guest suite on the main level provides exceptional comfort and privacy for visitors. Accessible by both a private spacious elevator and staircase, the second level is designed for elevated entertaining and relaxed living alike. A comfortable loft serves as a central gathering space surrounded by 3 beautifully appointed en-suite guest bedrooms. Additional features include impact-resistant doors and windows, whole-house 20- kilowatt generator and the highest level of craftsmanship and finishes throughout. An exceptionally rare offering in one of Naples’ most prestigious locations, this remarkable estate delivers unparalleled luxury, timeless architecture and the ultimate Olde Naples lifestyle just steps from the beach and world-class dining and shopping. This home offers you the convenience of living a life of walking to the beach every day, dining on Third Street, and enjoying the newly opened Olde Naples Hotel which offers a bar for an evening beverage after you enjoy the beautiful Naples sunsets.

160 Broad Avenue S, Naples

4 Beds ⋅ 5 Baths ⋅ Olde Naples SubDv.

PRICED AT LAND VALUE! LOWEST PRICED LISTING ON THE BEACH BLOCK IN ALL OF OLDE NAPLES — (Optional 50’ boat slip at the Cove Inn available for purchase with the property.) Opportunity knocks for a chance to own the ultimate beach cottage in one of Naples’ most coveted locations, just steps from the iconic Naples Pier and the white sugar-sand beaches of the Gulf. Privately tucked within lush tropical landscaping, this one-of-a-kind “Swiss-Family Robinson Treehouse” blends artistic charm with modern comforts, creating a secluded retreat in the heart of Olde Naples. Just a short stroll from the boutiques, fine dining, farmers markets, local parades and vibrant coastal lifestyle of 3rd Street South, the setting simply cannot be replicated. Designed for both relaxation and entertaining, the property showcases an incredible collection of unique indoor and outdoor spaces, including a heated swimming pool, private courtyard oasis, detached bar house with full kitchen, tranquil koi pond, infrared sauna, outdoor shower, and a raised covered “widow’s watch” seating area perfect for enjoying Naples sunsets, firework shows and coastal breezes. Additional highlights include a durable metal roof, back-alley access, oversized driveway for 5+ vehicles, and exceptional privacy throughout the property. Situated on a 77’ x 151’ lot, the possibilities are endless. Whether you envision renovating and enjoying the existing residence, creating a luxury custom estate, or developing a high-end investment property, this homesite offers extraordinary potential in a premier beach-block location right in the action of downtown Naples. Investors will appreciate the strong vacation rental and spec-home opportunities, while end users can create the ultimate private beach retreat just a few steps from the Gulf of Mexico. Adding to the long-term appeal, the newly reimagined Naples Pier is nearing completion, further enhancing the value and desirability of this exceptional location. A rare offering with unmatched character, location, and future potential — this is Olde Naples living at its finest. High and dry with no flooding waters entering the main residence.

61 12th Avenue S, Naples

4 Beds ⋅ 5 Baths ⋅ Olde Naples SubDv.

Accented with the color of morning-lit palms, this 2016 West Indies style home by Jeff Harrell and Associates offers a modern touch to the classic Naples charm. Located in the heart of Olde Naples, you’re on the doorstep of everything the city has to offer. Walking distance to 5th Avenue South and 3rd Street offers an endless variety of dining and shopping experiences. Boater? Naples Bay is a short walk away with the Naples Marina just across the street. Looking for the Beach? just head west. Find your spot in the sand with over 40 public beach access points to choose from. The home features 4 bedrooms, 4.5 baths and a 2 car garage. The open floor plan features beautiful hardwood flooring in each room, soaring ceilings, and floor-to-ceiling windows offering endless natural light. Perched at the Western end of Jumby Bay, this home stands out with unmatched privacy and extra space. It is the only residence in the development whose pool does not back up to another home, delivering a truly secluded outdoor area. In addition, 912 sits on a larger .19-acre lot compared to the .14-acre lots of central homes, creating a generous yard beside the pool. The chef’s kitchen is equipped with premium appliances including a Viking oven and cooktop, Miele refrigerator, Miele dishwasher, Miele convection microwave, and Uline wine cooler. A huge center island serves as the heart of the home, perfect for food preparation, casual dining, or buffet service. The lushly landscaped lanai is accessible from the great room and kitchen through multiple French doors, offering a covered and screened seating and dining area with cabana bath, plus a gas grill in the open space. Just beyond lies the sun-drenched 32-foot pool, spacious spa, and pergola-covered seating. This is the perfect spot for relaxing or entertaining day or night. Off the pool, you’ll find a private first-floor guest bedroom. On the second floor, The oversized master suite boasts dual walk-in closets designed for maximum functionality, a floating tub, and a large separate shower. Down the hall you’ll find a guest room with an en-suite bathroom and balcony. Above the garage and accessible from the main residence or a private alleyway entrance sits a versatile bonus space that can serve as a guest casita, office, or fitness center complete with a private bath. The HOA fee includes landscaping and pool maintenance, with weekly cleanings. On-street improvements also provide additional parking right on 9th Ave. Schedule your private showing today and make 912 9th Ave S. your new address in paradise!

912 9th Avenue S, Naples

6 Beds ⋅ 6 Baths ⋅ Olde Naples SubDv.

Experience the pinnacle of beachfront luxury from this extraordinary Naples coastal estate, where timeless Bermuda-inspired architecture meets effortless modern elegance. Perfectly positioned along 108 feet of pristine Gulf frontage, this six-bedroom residence offers an unparalleled opportunity to own a private sanctuary directly on the sugar-white sands of Naples. Evoking the refined charm of Alys Beach, the home’s striking white stucco exterior, parapet walls, and lush manicured landscaping create a serene and sophisticated coastal presence. Ideally located just steps from the new Four Seasons Naples Beach Club and moments from the boutiques and dining of downtown Olde Naples, the property offers a rare combination of privacy, prestige, and walkable convenience. Inside, expansive living spaces are bathed in natural light through walls of French doors that frame breathtaking panoramic views stretching from sand to sea. Thoughtfully designed for both grand entertaining and relaxed coastal living, the residence offers a seamless flow between formal and casual gathering spaces. A dramatic double living room and elegant dining area, complete with a custom beverage station and bar, create an unforgettable setting for hosting family and guests. The chef’s kitchen opens effortlessly to a warm and inviting family room and features a large center island, stone countertops, premium appliances, and a fully appointed butler’s pantry with wine refrigeration. Two luxurious primary suites—one on the main level and another upstairs with a private balcony overlooking the Gulf—provide tranquil retreats designed for ultimate comfort and privacy. A dedicated office on the main floor further enhances the home’s functionality for today’s lifestyle. Every detail throughout the residence reflects exceptional craftsmanship, timeless design, and understated sophistication. From the refined architectural elements to the seamless indoor-outdoor connection, this remarkable property embodies Naples beachfront living at its absolute finest.

23 6TH AVE N, Naples

4 Beds ⋅ 6 Baths ⋅ Olde Naples SubDv.

Discover an exquisite retreat in the heart of Olde Naples, just 2.5 blocks from 3rd Street South, featuring some of Naples’ most desirable shopping and dining experiences. Enjoy the sugar-white sands of the Gulf just moments away. This impeccably designed residence embodies refined coastal elegance, offering four lavish bedroom suites—each with a private ensuite bath and spacious walk-in closet—alongside a private study, stylish powder room and dedicated pool bath. Every detail has been thoughtfully curated, from the oversized four-car garage to the seamless indoor-outdoor living experience. An expansive covered lanai, complete with a fully appointed outdoor kitchen, frames the sparkling pool and creates a captivating setting for sunset dinners and sophisticated entertaining. A rare blend of luxury, comfort, and prime location—this is Naples living at its finest.

545 13th Avenue S, Naples

4 Beds ⋅ 6 Baths ⋅ Olde Naples SubDv.

Experience the epitome of luxury living in this exceptional new construction home, perfectly situated in the heart of Olde Naples. Crafted by Refined Builders, this remarkable residence presents a rare opportunity to own a true masterpiece in one of Naples’ most coveted locations. Ideally positioned just minutes from the world-class dining and shopping of 5th Avenue South and 3rd StreetSouth, as well as Naples’ iconic beaches, this 4-bedroom + den, 5.5-bath home offers the perfect blend of luxury, comfort, and convenience—complemented by tranquil lake views from the 2nd floor and lush tropical landscaping. Wide-plank European oak floors and tongue-and-groove ceilings set a sophisticated tone, while the expansive great room flows seamlessly into a stunning gourmet kitchen featuring a quartz-clad center island, sleek two-tone cabinetry, and a full suite of premium Thermador appliances—ideal for both everyday living and elegant entertaining. Sliding glass doors lead to your private outdoor sanctuary, complete with a resort-style saltwater pool and spa, custom summer kitchen, and a spacious covered lanai—perfect for seamless indoor-outdoor living. The first-floor primary suite is a luxurious retreat with direct pool access and a spa-inspired bath featuring a soaking tub, oversized walk-in shower, and dual vanities. Upstairs, three ensuite guest bedrooms—including a VIP second master—are accessible via stairs or a private elevator. A bonus living room with wet bar, scenic balcony, and captivating lake views provides a relaxed space to unwind or entertain. Additional highlights include dual laundry rooms, a 3-car garage, tankless water heater, whole-house generator, and propane tank.

493 8th Avenue S, Naples

5 Beds ⋅ 4 Baths ⋅ Olde Naples SubDv.

Ideally located in the heart of Olde Naples, this beautifully renovated five-bedroom, four-bath Key West–style residence offers an exceptional blend of coastal charm and walkable luxury. Just steps from Fifth Avenue South, Gulf beaches, and directly across from Cambier Park. The residence features a spacious open floor plan with vaulted ceilings, Miami-Dade pine floors, and timeless beadboard details. The living, dining, and kitchen areas flow seamlessly, creating an ideal setting for both relaxed coastal living and elegant entertaining with room for large family gatherings. Recent improvements include a new standing seam metal roof and a new main air conditioning system installed in 2025, offering enhanced durability, efficiency, and peace of mind. Outdoor living is highlighted by a heated swimming pool, multiple lounge and grassy lawn areas. This is a rare opportunity to own a classic coastal home in a premier walk-to-everything location in Olde Naples. Excellent rental history.

660 8th Avenue S, Naples

5 Beds ⋅ 7 Baths ⋅ Olde Naples SubDv.

Steps from the shimmering Gulf waters, pristine white-sand beaches, and the vibrant charm of 5th Avenue South and 3rd Street South, 264 8th Avenue South offers the ultimate Olde Naples lifestyle—where prime location, refined luxury, and effortless living converge. Designed by Beck Architectural Group, this stunning home sits on a premium southern-exposure lot in the heart of Olde Naples. The thoughtfully designed floor plan prioritizes main-level living, featuring an expansive great room, a chef’s kitchen, a luxurious primary suite, and a versatile private flex bedroom—ideal for guests, a home office, or a wellness space. Seamless indoor-outdoor flow leads to a private backyard retreat designed for year-round enjoyment. The covered outdoor living area is outfitted with a gourmet kitchen featuring a Lynx grill, refrigerated drawers, and a prep sink, along with a living space anchored by a feature wall with a television and gas fireplace. Beyond, the sun-drenched, fenced backyard is maximized with a large saltwater pool with a sun shelf, water features, and an integrated spa, all surrounded by ample deck space for lounging, low-maintenance turf for pets, and an outdoor shower. The designer kitchen by Design West is a true showpiece, appointed with custom cabinetry and top-of-the-line appliances, including a Wolf induction cooktop and oven; Sub-Zero refrigeration with wine storage and auxiliary beverage drawers; a Cove dishwasher; and Cristallo quartzite countertops. The adjacent butler’s pantry enhances functionality with additional prep space, a Wolf six-burner gas range, Wolf microwave, Asko dishwasher, and a generous walk-in pantry—perfectly tucked away for effortless entertaining. The main-level primary suite is a private sanctuary, featuring a vaulted ceiling, tranquil backyard views, and a spa-inspired bath with dual vanities, separate water closets, a soaking tub, a walk-in shower, and an oversized custom closet. Upstairs, three spacious bedrooms each offer en suite baths, complemented by a shared media room with a breakfast bar and private deck—an ideal vantage point for breathtaking western sunsets and seasonal fireworks. Throughout the home, rich hardwood flooring, custom retractable privacy shades, and refined architectural details—including 11-inch baseboards—create a sophisticated and cohesive aesthetic. Additional features include dual laundry rooms; a three-car garage with rear alley access and sufficient height to accommodate lifts in two bays; natural gas; a whole-house generator; water filtration and humidification systems; a private elevator; Lutron lighting; surround sound; and full home automation. The property is also situated on the same power grid as a nearby fire station, offering added peace of mind. This exceptional residence perfectly blends Olde Naples elegance with modern luxury—ideal for those seeking the very best in coastal living, location, and sophisticated design.

264 8th Avenue S, Naples

3 Beds ⋅ 3 Baths ⋅ Olde Naples SubDv.

This charming coastal cottage offers an unbeatable location just moments from the beach and the world-class dining and shopping of 5th Avenue South. Embrace the quintessential Naples lifestyle—highly walkable and perfect for biking or golf cart cruising—right from your doorstep. Inside, the home showcases a fresh coastal contemporary design with thoughtful updates throughout, creating a light, inviting atmosphere. Step outside to your private backyard retreat, where a desirable southern exposure fills the pool area with sunshine all day. The outdoor space has been beautifully enhanced with all new landscaping, stylish new Polywood furniture, a new pool umbrella, and new pool lighting, all complementing the recently repainted exterior. Entertain with ease in the covered lanai and built-in outdoor kitchen, or enjoy the expansive side yard featuring a generous grassy dog run—ideal for pet lovers. The well-designed floor plan offers both a living room and a separate family room, a spacious primary suite, skylights for added natural light, and a large U-shaped kitchen that seamlessly connects the dining and family areas. Built with quality in mind, the home features durable cement siding and remained high and dry with no water intrusion during recent hurricanes—offering true peace of mind. Additional highlights include a circular driveway for ample front parking and a detached oversized one-car garage with convenient alley access. This is a rare opportunity to own an adorable, move-in-ready home in one of Naples’ most sought-after neighborhoods—don’t miss it.

740 5th Avenue N, Naples

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