Olde Naples Homes with Courtyard Exterior Features

Welcome to Olde Naples, a charming gem nestled in the heart of Naples, Florida. This historic neighborhood is renowned for its picturesque streets lined with lush palm trees, vibrant bougainvillea, and a delightful mix of boutique shops, art galleries, and gourmet restaurants. The area exudes a timeless elegance, where the laid-back coastal lifestyle meets sophisticated charm. Residents and visitors alike enjoy leisurely strolls along the pristine beaches, just a stone's throw away, or savoring the stunning sunsets that grace the horizon.

One of the standout features of homes in Olde Naples is their inviting courtyard exteriors. These beautifully designed properties often boast private courtyards, creating a serene oasis that invites relaxation and outdoor living. Imagine sipping your morning coffee in a sun-drenched courtyard, surrounded by tropical landscaping, or hosting a delightful evening gathering under the stars. The courtyard designs not only enhance the aesthetic appeal of the homes but also provide a seamless blend of indoor and outdoor living, perfect for the Florida lifestyle.

The architectural styles in Olde Naples are as diverse as its residents, ranging from charming bungalows to luxurious estates, each with its unique character. The sense of community is palpable here, with neighbors often gathering for local events and enjoying the vibrant cultural scene that Naples has to offer. With its rich history, stunning natural beauty, and welcoming atmosphere, Olde Naples is not just a place to live; it’s a lifestyle waiting to be embraced. Discover your dream home in this idyllic neighborhood today!

Newest Olde Naples Homes with Courtyard Exterior Features

$6,300,000

4 Beds ⋅ 5.5 Baths ⋅ 226024974 MLS

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 AVE S, Naples

$1,870,000

2 Beds ⋅ 2 Baths ⋅ 226027036 MLS ⋅ Olde Naples BLDG.

Experience the pinnacle of downtown living at 365 5th Ave S, Unit 307, where the vibrant energy of Naples meets sophisticated coastal elegance. Located right in the heart of the iconic 5th Avenue South district and only two blocks from the beach, this residence places world-class dining, high-end boutiques, and sugar-sand beaches just moments from your front door. In the heart of the action but offering quiet solitude as it does not face 5th Ave South. Inside, the space feels bright and airy, with an open-concept layout designed for both effortless entertaining and quiet relaxation. Large windows invite an abundance of natural light to dance across the polished finishes, while the private balcony offers a perfect perch to soak in the tropical breeze and the rhythmic hum of the city below. The kitchen is a chef’s dream, featuring sleek cabinetry, premium appliances, and ample counter space for preparing coastal-inspired meals. The primary suite serves as a serene retreat, complete with a spa-like ensuite bathroom and generous closet space. Every detail in this home has been curated for those who appreciate a lifestyle of convenience and luxury. Whether you're enjoying a sunset dinner at a nearby bistro or spending a slow afternoon by the Gulf, this property offers an unparalleled opportunity to live where everyone else vacations. This is more than just a home; it’s your front-row seat to the very best of Naples.

365 5th AVE S Unit 307, Naples

$389,000

1 Beds ⋅ 1 Baths ⋅ 226026571 MLS ⋅ 960 On Seventh BLDG.

The absolute very best of the Naples beach lifestyle. Where to start, first of all you are literally down the street from the beach. A short 5 minute walk or 2 minute bike ride straight to one of the best beaches in the world and the Crown Jewel of Naples. As were talking about the proximity of the beach you also down the street from Naples very own 5Th ave and next to Cambier Park that sits on 12.84 acres that include the Norris Community Center, Five Lighted Shuffleboard Courts, One Bocce Courts, Lighted Basketball Court, Arthur L. Allen Tennis Center, Bandshell, Unique Children's Playground, Softball Field, Covered Pavilion and Lots of Open Green Space to Enjoy a Picnic. Cambier Park hosts a variety of ongoing entertainment and cultural activities at the downtown bandshell and the Norris Community Center. Signature seasonal art festivals, live musical performances, and weekend concerts are held in the park. Cambier park is right next to all of Naples finest dining, shopping, art gallery's, banking and cafes on 5Th Ave. There literally is no better location in the heart of Naples than this quaint beach condo. Now you know a little about the location let me tell you about the condo, the first thing you will notice is the building has a real 90210 vibe. A Mediterranean design with an open court yard featuring fountains and palm trees with a total of only 12 units. This building must be seen to appreciate just how calm the feeling is every time you enter, filled with nesting birds, Palm trees and the sound of the fountains make it the perfect place to come home to or the ultimate getaway location to unwind. This condo has not been lived in or used as a rental it was purchased for one specific reason, to create the perfect getaway, from it all. A home away from home. With that in mind the best way to create the dream beach getaway is to start from scratch and do it your way. So with that in mind no expense was spared and a complete gut job was done, well over $125,000.00 was spent on the renovations and an additional $20,000.00 on furnishings. Its all new, new ac, tile floors, bathroom, stainless appliances, washer and dryer, new kitchen with soft close draws, Quartz counter top and the list goes on. Basically everything from the lights to the floors and everything in-between is new. And it was used on random weekends for a quick getaway, this condo is showroom ready in new condition all anyone needs to bring is their tooth brush and you're good to go. You don't even need a car you can walk or bike everywhere it's all right outside your door. There are also additional storage units in the building to store your bikes or beach chairs. With the total amount of money spent close to $150,000.00 and the attention to detail and quality materials used not to mention the location, I think you will see why this truly is the perfect little beach getaway. 1 PET ALLOWED!

960 7th ST S Unit 105, Naples

$280,000

1 Beds ⋅ 1 Baths ⋅ 226026018 MLS ⋅ Twin Palms BLDG.

One of the best opportunities to own in the heart of Olde Naples! Beautifully renovated from top to bottom, this first-floor 1-bedroom, 1-bath residence combines timeless coastal style with an unbeatable location—all for just $280,000. The bright, open floor plan features wood-look porcelain tile flooring throughout, recessed lighting, a stunning custom kitchen with quartz countertops, stainless steel appliances, a designer tile backsplash, abundant cabinetry, and a beautifully remodeled bathroom with an oversized walk-in shower. Every detail has been thoughtfully selected to create a sophisticated, move-in-ready retreat. Located at 780 10th Avenue South, this charming condominium places you just a short stroll from both 5th Avenue South and 3rd Street South, where you'll enjoy award-winning restaurants, boutique shopping, art galleries, cafés, and entertainment. Naples' world-famous white-sand beaches are also just minutes away. Whether you're searching for your own Olde Naples getaway, a home for a young professional, comfortable guest accommodations for family and friends, or an investment opportunity, this residence offers exceptional value in one of Naples' most sought-after neighborhoods. Beautifully renovated. Prime Olde Naples location. Exceptional value. Rarely does an opportunity like this come along under $300,000.

780 10th AVE S Unit 1, Naples

$549,900

1 Beds ⋅ 1 Baths ⋅ 226025950 MLS ⋅ Castleton Gardens BLDG.

Welcome to Castleton Gardens 204, a rare second floor renovated and beautifully furnished one-bedroom condominium in the heart of Old Naples. This unit features a king-sized bedroom, updated bath, open kitchen with large island and a comfortable living space. Ideally just three blocks to 5th Avenue South, two blocks to Cambier Park and one block to Tin City, with Naples beaches less than a mile away. Ideal for owners and investors, the community allows rentals up to 12 times per year with a 30-day minimum. Amenities include a heated pool, spa and barbecue area set within a charming banyan tree-lined courtyard. Exterior stair access with no elevator! Castleton Gardens 204 presents a rare opportunity to own a turnkey property that captures the essence of Naples living while delivering exceptional versatility.

980 7th AVE S Unit 204, Naples

$425,000

1 Beds ⋅ 1 Baths ⋅ 226024514 MLS ⋅ Garden Court BLDG.

Positioned in the heart of Old Naples, this beautifully updated residence presents an exceptional opportunity to embrace one of Southwest Florida's most coveted coastal lifestyles. Located just three blocks from the sugar-white sands of the Gulf and within an effortless stroll of both 5th Avenue South and 3rd Street South, you'll enjoy world-class dining, boutique shopping, art galleries, and vibrant entertainment right outside your door. Bathed in natural light, this desirable second-floor end residence offers a bright, airy ambiance enhanced by tasteful neutral finishes, impact-resistant windows and doors, central air conditioning, and the convenience of an in-residence washer and dryer. Just beyond the living space, a private sun-drenched open-air patio provides the perfect setting to enjoy your morning coffee or unwind amid the gentle coastal breezes. Nestled within the intimate Garden Court community, this charming three-building enclave surrounds a lush, tranquil courtyard, creating a peaceful retreat just moments from the energy of downtown Naples. Whether you're seeking a seasonal getaway, investment opportunity, or year-round residence, this rare offering delivers the quintessential Old Naples lifestyle—where pristine Gulf waters, breathtaking sunsets, and endless opportunities for dining, shopping, and recreation are all just a short walk away. Leasing is permitted up to three times per year with a 30-day minimum. Please note that pets are not permitted. One parking space comes with unit.

285 8th AVE S Unit 285, Naples

$375,000

1 Baths ⋅ 226021422 MLS ⋅ Cove Inn BLDG.

Rarely does an opportunity arise to own a waterfront retreat in the heart of Old Naples with the flexibility to enjoy personally and rent on a nightly, weekly, monthly or seasonal basis. Along Naples Bay at The Cove Inn, this updated residence offers an ideal combination of lifestyle, convenience and income-producing potential. Overlooking the marina and Naples Bay, the property embraces the boating lifestyle that makes Naples so desirable. The adjacent marina offers direct Gulf access, and boat slips may be available for lease or purchase separately, subject to availability. Spend your days on the water, then return home to spectacular sunsets, sparkling bay views and the tranquil sight of yachts cruising through the harbor. Thoughtfully renovated and well maintained, the residence features wood-plank tile flooring throughout, a beautifully updated kitchen and bath, and coastal-inspired finishes highlighted by stunning aqua mother-of-pearl tile accents. Light, bright and move-in ready, the property has been gently enjoyed by its owner and presents in excellent condition. An oversized lounge chair conveniently converts into an additional bed in moments, providing comfortable accommodations for overnight guests. Ownership includes automatic membership to the legendary Chickee Bar, a Naples waterfront institution where residents and guests gather to enjoy tropical cocktails, unforgettable sunsets overlooking the marina. Additional amenities include a large resort-style pool with abundant lounge seating, a recently renovated lobby opening to a sun-filled waterfront patio, and a welcoming fire pit overlooking Naples Bay. From holiday fireworks to the beloved Naples Christmas Boat Parade, the waterfront setting provides a front-row seat to some of Naples cherished traditions. Just moments from Fifth Avenue South, residents can enjoy world-class dining, boutique shopping, art galleries and entertainment less than a half mile away, easily accessed by foot or via the complimentary Cove Inn trolley. Two waterfront seafood restaurants are adjacent to the property, while the popular Cove Inn Coffee Shop offers a place to begin each morning before another day in paradise. Recognizing the value of preparedness in a waterfront setting, the owner has thoughtfully equipped the residence with a storm management package that includes custom Garrison flood planks for the sliding glass doors and advanced reusable water-activated flood control barriers. Designed for quick deployment and convenient storage, these improvements provide an added measure of confidence and will convey with the property. Low quarterly dues even include electric! Whether you're searching for a seasonal escape, waterfront pied-à-terre, income-producing investment, or a combination of all three, this exceptional residence offers the quintessential Old Naples lifestyle in one of the area's iconic waterfront destinations.

900 Broad AVE S Unit 125, Naples

$6,450,000

4 Beds ⋅ 4.5 Baths ⋅ 226019479 MLS

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 AVE S, Naples

$625,000

1 Beds ⋅ 1 Baths ⋅ 2026017700 MLS ⋅ Kensington Gardens BLDG.

Location, location, location in the heart of Olde Naples! Welcome to Kensington Gardens, a charming vacation rental community just one block from world-famous Fifth Avenue South and only a short stroll to the white sandy beaches of the Gulf of Mexico. This beautifully updated 1-bedroom, 1-bath condominium offers the perfect Naples retreat with a bright coastal feel, tasteful furnishings, ceramic tile throughout, and in-residence laundry for added convenience. Situated in one of Naples’ most walkable and desirable downtown locations, guests can enjoy easy access to upscale dining, boutique shopping, art galleries, live entertainment, cafés, and local favorites throughout Fifth Avenue South and nearby Third Street South. Kensington Gardens offers classic Olde Naples charm with a relaxed atmosphere, making it ideal as a seasonal getaway, investment property, or personal vacation escape. Owner has a recent inspection report available. Property is being sold AS IS, and reasonable offers will be considered.

480 5th ST S Unit 202, Naples

$1,525,000

2 Beds ⋅ 2 Baths ⋅ 226019603 MLS ⋅ Eight Fifty Central BLDG.

A rare top-floor end-unit at Eight Fifty Central, this two-bedroom, two-bath residence offers a clean, modern design within a low-density, highly sought-after Olde Naples address. Built in 2021 and comprised of just 22 residences, the building delivers both exclusivity and everyday convenience. The interior is defined by an open-concept layout where the living and dining spaces transition effortlessly into a gourmet kitchen outfitted with quartz countertops, a natural gas Wolf range and Sub-Zero appliances. Elevated ceilings and expansive impact glass invite abundant natural light, while a private balcony extends the living space outdoors. Both bedrooms are generously sized and filled with natural light, offering flexibility to accommodate a variety of design styles or uses. The residence is offered furnished, providing a true turnkey opportunity. Residents enjoy a thoughtfully curated amenity package including an interior pool deck, lush courtyard green space and a rooftop outdoor patio featuring a built-in grill, fire pit and multiple seating areas designed for relaxation and entertaining. Ideally at the corner of 8th Street South and Central Avenue, just near dining, shopping and entertainment of 5th Avenue South and minutes to Naples iconic beaches, this property captures the essence of luxury, privacy and downtown accessibility in one exceptional offering.

850 Central AVE Unit 311, Naples

$349,900

2 Beds ⋅ 1 Baths ⋅ 226019202 MLS ⋅ Bayview BLDG.

PRICED TO SELL! FULLY UPDATED 1ST FLOOR END UNIT WITH METAL ROOF IN DOWNTOWN NAPLES! Prime location in highly desirable Olde Naples, just steps from 5th Avenue South, Cambier Park, and the white sand beaches of the Gulf, this beautifully updated 2-bedroom condo offers exceptional value in a neighborhood surrounded by multimillion-dollar residences. Now offered at a newly improved price, this is an outstanding opportunity to own in one of Naples' most coveted locations. This WEST-FACING END UNIT enjoys beautiful sunset views and an abundance of natural light while maximizing quiet, private living. The entire condo has been extensively updated with high-end finishes throughout, including NEW FLOORING, a RENOVATED KITCHEN with QUARTZ COUNTERTOPS, a sleek tile backsplash, STAINLESS STEEL APPLIANCES, UPGRADED CEILING FANS & LIGHT FIXTURES, and NEW CLOSET DOORS — creating a clean, modern, move-in-ready feel. Additional peace of mind comes from custom removable flood gates, newer HVAC and Water Heater (2022), along with a METAL ROOF & GUTTERS (2024). The exterior has been FRESHLY PAINTED and is beautifully maintained, with lush landscaping that enhances the community's peaceful, inviting atmosphere. With VERY LOW HOA FEES and a sought-after Olde Naples location close to beaches, shopping, dining, and downtown attractions, this condo is ideal for full-time living, a seasonal retreat, or an investment opportunity. Schedule your showing today! THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER — INQUIRE FOR MORE DETAILS. ** (Renderings that showcase furniture have been virtually staged)

975 9th AVE S Unit 11, Naples

$494,000

1 Beds ⋅ 1 Baths ⋅ 226019237 MLS ⋅ Garden Court BLDG.

Steps from the beach and all of Naples’ finest dining! This beautiful, turnkey furnished condo offers an unbeatable location - 2.5 blocks to prestigious Fifth Avenue and the beach, and 4 blocks to the charming boutiques and restaurants on Third Street South! This unit is filled with natural light and set within an intimate boutique community. Unit had NO WATER DAMAGE during any of the last hurricanes/storms. It also features new impact-resistant windows, a newer A/C and water heater, an updated kitchen and bath, and easy-to-maintain tile flooring throughout. Tastefully furnished and decorated in a coastal contemporary theme, complete with a sleeper sofa ideal for additional guests or family. Enjoy your private southern-facing patio which overlooks a peaceful garden courtyard. The community offers common laundry, extra storage, bike racks, and recent updates include new exterior paint, gutters, soffits, pavers, irrigation, and landscaping.

275 8th AVE S Unit 275, 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.