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$300,000
226026722 MLS
One or more photo(s) has been virtually staged, AI generated or rendered. Welcome to The St. Croix House model at The Island Cottages in The Bayshore Arts District - a special family of Olde Florida Contemporary custom designed single family homes on Jeepers Drive. In the last 10 years, the Developer/Designer of these cottages has worked individually with 11 new owners to fashion this unique vintage urban environment at the Heart of The Bayshore Arts District adjacent to The Bayshore/Sugden Park Boardwalk and Lake Avalon’s white sand beach and sailing center. These new residences will be constructed by Naples’ renowned local builder, Gulfstream Homes. All the Cottages in The Island Cottages in The Bayshore Arts District have been given names by their owners. These names are by agreement designated as memorializing a favorite island which is important to the owners. Further, in every case the homes are decorated with a historic “Quarterboard” sign with the name and a matching house number sign designating thee Jeepers Drive house number The St Croix House model is the ultimate outdoor living cottage in almost 2000 square feet of living space under air conditioning. A welcoming front porch which leads you into a lovely vestibule and private office which then leads to the great room (large kitchen, dining and living room with an adjoining powder room) and continues onto the huge covered lanai. Breakfast on the porch, cocktails on the lanai, and relaxing in the pool and spa in the private backyard sanctuary and garden. There are 3 bedrooms. The premier suite is downstairs with ensuite bath and walk-in closets with direct access to the lanai and the backyard. There are 2 guest bedrooms on the sunny 2nd floor plus 3 1/2 baths, a great laundry, a 2 car drive-through garage with access to the back yard. The concept is to offer the new owner the opportunity to personalize the design by selecting all interior finishes creating a space that perfectly reflects your style and taste and to custom design the outdoor living areas to include pool, spa, gardens, patios, outdoor cooking areas etc. Whether you’re seeking a full time residence, seasonal retreat or investment property, these Island Cottages offer the ideal combination of luxury, style, flexibility and location. Perfectly positioned at the vibrant center of Naples’ most unique downtown village, The Bayshore Arts District, you’ll enjoy the convenience of walking, biking or boating to local restaurants, cafes, breweries, wine bars, boutiques and neighborhood shops as well as The Naples Botanical Garden, The Naples Bay Boat launch and the National Pickleball Center. Around Naples Bay, 5th Avenue is just 5 minutes away with 3rd Street shopping and the Naples Beaches just beyond that. With new homes and exciting development continuing to transform the area, this is an opportunity to own a brand new home, a vintage Island Cottage, in Naples fastest growing, most unique and exciting waterfront neighborhood.

114 - A JEEPERS DR, Naples

Courtesy of John R Wood Properties.

$350,000
226026707 MLS
One or more photo(s) has been virtually staged, AI generated or rendered. Welcome to Grand Turk Island Cottage at The Island Cottages in The Bayshore Arts District - a special family of Olde Florida Contemporary custom designed single family homes on Jeepers Drive. In the last 10 years, the Developer/Designer of these cottages has worked individually with 11 new owners to fashion this unique vintage urban environment at the Heart of The Bayshore Arts District adjacent to The Bayshore/Sugden Park Boardwalk and Lake Avalon’s white sand beach and sailing center. These new residences will be constructed by Naples’ renowned local builder, Gulfstream Homes. All the Cottages in The Island Cottages in The Bayshore Arts District have been given names by their owners. These names are by agreement designated as memorializing a favorite island which is important to the owners. Further, in every case the homes are decorated with a historic “Quarterboard” sign with the name and a matching house number sign designating thee Jeepers Drive house number. Grand Turk Island Cottages features 4 bedroom + office, 3 1/2 bath in almost 2800 square feet of living space. The steep silver metal double roofed gable invites you up to the friendly front porch and into the lovely front door to a two-story masterpiece. Inside, the main arcade takes you to the sunny private office, a half bath, a coat closet and access to the 3-car garage before arriving at the huge wide great room. You’ll be looking through the very large kitchen, living and dining areas, through the covered, screened lanai to the the amazing pool and spa patio and the tropical landscaping in the backyard sanctuary. The first floor premier bedroom suite is adjacent along the whole left side of the cottage. It includes a large bedroom and adjoining porch with access to the pool and a private outdoor shower. The suite continues toward the front of the home into the full bath with 2 sinks, shower, free standing bath tub and lavatory leading to a large walk-in closet and finally the laundry. The upstairs has 3 additional bedrooms with beautiful views, two full baths, an office/craft room as well an exercise room. This Island Cottage is truly exceptional!

144 - A JEEPERS DR, Naples

Courtesy of John R Wood Properties.

$1,295,000
3 Beds ⋅ 3 Baths ⋅ 226024464 MLS
Welcome to Morgan Island Bungalow model at The Island Cottages in The Bayshore Arts District - a special family of Olde Florida Contemporary custom designed single family homes on Jeepers Drive. In the last 10 years, the Developer/Designer of these cottages has worked individually with 11 new owners to fashion this unique vintage urban environment at the Heart of The Bayshore Arts District adjacent to The Bayshore/Sugden Park Boardwalk and Lake Avalon’s white sand beach and sailing center. These new residences will be constructed by Naples’ renowned local builder, Gulfstream Homes. All the Cottages in The Island Cottages in The Bayshore Arts District have been given names by their owners. These names are by agreement designated as memorializing a favorite island which is important to the owners. Further, in every case the homes are decorated with a historic “Quarterboard” sign with the name and a matching house number sign designating thee Jeepers Drive house number. The Morgan Island Bungalow model offers the new owner the option of joining this unique street at starter home pricing by initially building only the stunning main house of 2421 gross square feet (1422 sq ft of air-conditioned interiors) with the option to add additional structures and/or amenities as time moves along. The large neighborly signature front porch leads to the great room (living room, dining room and kitchen). This economical one level layout includes 3 ensuite bedrooms with the larger premier suite opening on to a sweet covered lanai at the private back yard. There is an optional 2 car garage/shop/boat storage area to the side. The yard is spacious, a “blank canvas”, as you will, leaving room to develop a pool, patio, or additional future in-law or guest, home office or Air B&B new construction. Opportunity to personalize the design by selecting all interior finishes creating a space that perfectly reflects your style and taste and to custom design the outdoor living areas to include pool, spa, gardens, patios, outdoor cooking areas etc. Whether you’re seeking a full time residence, seasonal retreat or investment property, these Island Cottages offer the ideal combination of luxury, style, flexibility and location. Perfectly positioned at the vibrant center of Naples’ most unique downtown village, The Bayshore Arts District, you’ll enjoy the convenience of walking, biking or boating to local restaurants, cafes, breweries, wine bars, boutiques and neighborhood shops as well as The Botanical Garden, The Naples Bay Boat launch and the National Pickleball Center. Around Naples Bay, 5th Avenue is just 5 minutes away with 3rd Street shopping and the Naples Beaches just beyond that. With new homes and exciting development continuing to transform the area, this is an opportunity to own a brand new home, a vintage Island Cottage, in Naples fastest growing, most unique and exciting waterfront neighborhood.

114 JEEPERS DR, Naples

Courtesy of John R Wood Properties.

$1,695,000
4 Beds ⋅ 3.5 Baths ⋅ 226024462 MLS
One or more photo(s) has been virtually staged, AI generated or rendered. Welcome to Antigua Island House model at The Island Cottages in The Bayshore Arts District - a special family of Olde Florida Contemporary custom designed single family homes on Jeepers Drive. In the last 10 years, the Developer/Designer of these cottages has worked individually with 11 new owners to fashion this unique vintage urban environment at the Heart of The Bayshore Arts District adjacent to The Bayshore/Sugden Park Boardwalk and Lake Avalon’s white sand beach and sailing center. These new residences will be constructed by Naples’ renowned local builder, Gulfstream Homes. All the Cottages in The Island Cottages in The Bayshore Arts District have been given names by their owners. These names are by agreement designated as memorializing a favorite island which is important to the owners. Further, in every case the homes are decorated with a historic “Quarterboard” sign with the name and a matching house number sign designating thee Jeepers Drive house number. The Antigua Island House model is an outdoor-living dream! It features a large friendly front porch, a huge open concept great room (Kitchen, dining and living) and a generous screened lanai on the first level, 4 bedrooms (2 premier and 2 guest) on the mezzanine and 2nd level with 2 private decks and 3 1/2 baths. Antigua House is a total build of 3474 square feet of which 2341 square feet are interior air conditioned spaces. The site layout provides for parking for 5 cars with 2 in the garage. The concept is to offer the new owner the opportunity to personalize the design by selecting all interior finishes creating a space that perfectly reflects your style and taste and to custom design the outdoor living areas to include pool, spa, gardens, patios, outdoor cooking areas etc. Whether you’re seeking a full time residence, seasonal retreat or investment property, these Island Cottages offer the ideal combination of luxury, style, flexibility and location. Perfectly positioned at the vibrant center of Naples’ most unique downtown village, The Bayshore Arts District, you’ll enjoy the convenience of walking, biking or boating to local restaurants, cafes, breweries, wine bars, boutiques and neighborhood shops as well as The Naples Botanical Garden, The Naples Bay Boat launch and the National Pickleball Center. Around Naples Bay, 5th Avenue is just 5 minutes away with 3rd Street shopping and the Naples Beaches just beyond that. With new homes and exciting development continuing to transform the area, this is an opportunity to own a brand new home, a vintage Island Cottage, in Naples fastest growing, most unique and exciting waterfront neighborhood.

144 JEEPERS DR, Naples

Courtesy of John R Wood Properties.

$929,000
4 Beds ⋅ 3 Baths ⋅ 226016331 MLS
One or more photo(s) has been virtually staged, AI generated or rendered. Welcome to 176 Jeepers Dr, a beautifully designed new construction home located in the heart of Naples’ vibrant Bayshore Arts District. Offering 4 bedrooms and 3 bathrooms, this residence seamlessly blends modern design with relaxed coastal living. The home welcomes you with a metal roof, paver driveway, and a covered front porch accented by classic white railing, creating warm and inviting curb appeal. Built with impact-resistant windows, doors, sliding glass doors, and garage door, and elevated 9 feet above base elevation, it provides durability, added protection, and long-term value. Inside, the open-concept layout is enhanced by tray ceilings, recessed lighting, and continuous wood-look flooring throughout. The kitchen is both elegant and functional, featuring quartz countertops, custom cabinetry, stainless steel appliances, and a spacious center island perfect for gathering and entertaining. A desirable split-bedroom floor plan offers privacy, while the primary suite serves as a relaxing retreat with abundant natural light and direct access to the lanai. Step outside to the covered lanai, complete with a ceiling fan—an ideal space for year-round outdoor living. The backyard provides ample room to design your own custom pool, with a permit already submitted by the current owner, offering added convenience and future potential. Enjoy a prime location just minutes from downtown Naples and the Gulf beaches, while immersed in the vibrant energy of the Bayshore area. Discover the beauty of Naples Botanical Garden, unwind at Celebration Park Naples, or dine at favorites like The Real Macaw, Rebecca's Wine Bar, and The Med. The neighborhood also offers art galleries, boutique shopping, cafés, and live entertainment. Nearby, East Naples Community Park features world-class pickleball, tennis courts, scenic walking trails, and easy access to the Bayshore Drive boardwalk connecting to Sugden Regional Park. With no HOA fees and an exceptional location, this home presents a rare opportunity for both homeowners and investors.

176 Jeepers DR, Naples

Courtesy of Downing Frye Realty Inc..

$283,500
4 Beds ⋅ 2 Baths ⋅ 225012976 MLS
Coastal living meets investment opportunity in this charming 4-bedroom, 2-bathroom manufactured home in Naples' desirable Bayshore Arts District! Just 5 minutes from downtown Naples, enjoy world-class beaches, restaurants, and boutiques. Located in the sought-after Island Cottages on Jeepers neighborhood, this home offers a warm, community-focused atmosphere. The area is being revitalized by G.J. Gardner Homes with custom, island-inspired designs. Walkable to all the Bayshore Arts District has to offer – art galleries, restaurants, and more – this property also boasts NO HOA FEES! Embrace the vibrant lifestyle of the Bayshore Arts District with its eclectic mix of attractions. Explore the Naples Botanical Garden, indulge at Celebration Food Truck Park, and savor culinary delights at The Real Macaw, Rebecca's, The Med, and other local favorites. Discover unique boutiques, cafes, coffee shops, and art galleries, and enjoy live music venues. Just moments away, the East Naples Community Park awaits, a hub for adult and youth activities. Pickleball enthusiasts will rejoice with 64 courts, home to the US Open Pickleball Championship! A 3/4-mile jogging trail and scenic lake with picnic area complete this exceptional location. This rare opportunity combines luxury, charm, and value in one of Naples' most dynamic neighborhoods

162 Jeepers DR, Naples

Courtesy of KW Elevate Luxury.

Selling Office: Premiere Plus Realty Company.

$1,060,000
3 Beds ⋅ 2 Baths ⋅ 225005036 MLS
Welcome to a coastal-inspired dream home in the heart of the Bayshore Arts District! Built in 2020, this custom home is a masterpiece of modern design and craftsmanship. With a metal roof and hurricane impact-resistant doors and windows, this property is built to provide peace of mind and style. The star of the show? Your private saltwater pool and spa, complete with an outdoor shower on an expansive screened lanai—perfect for relaxing or entertaining in true Florida fashion. Step inside and be wowed by the chef’s kitchen featuring a 12-foot custom quartz island, matte GE Café appliances, a convection oven, and an induction stovetop—designed for both beauty and functionality. Located in the highly desirable Island Cottages on Jeepers neighborhood, this home offers an amazing location within the Bayshore Arts District. Designed as a throwback to the old days, this charming seaside-inspired community celebrates front porches as the highlight of every home, creating a warm and inviting atmosphere where neighbors can interact daily and enjoy a true sense of community. The neighborhood is being redesigned and built by G.J. Gardner Homes, with each home custom-built and inspired by the islands. Best of all, it’s walkable to everything the Bayshore Arts District has to offer, including art galleries, restaurants, and more. One of the most exceptional features of this property? There are no HOA fees! That means no additional monthly expenses. Opportunities like this are incredibly rare, especially in a community this desirable. It’s a true win for those looking for luxury, charm, and value. Living in the Bayshore Arts District means embracing one of Naples’ most vibrant and creative areas. Discover the Naples Botanical Garden, Celebration Food Truck Park, and incredible dining options like The Real Macaw, Rebecca’s, The Med and more. Stroll through locally owned boutiques, charming cafes, coffee shops, and art galleries, or enjoy live music at one of the many venues nearby. Just around the corner is the vibrant world of the East Naples Community Park, where excitement and fun await visitors of all ages! Nestled in the heart of the Bayshore Arts District, this bustling park serves as a dynamic hub for a plethora of adult and youth activities. This park is Pickleball Central with 64 Pickleball courts and home to the renowned US Open Pickleball Championship! There are also lighted basketball courts, tennis courts, racquetball courts, lighted softball, and soccer fields. There is also a 3/4 mile jogging trail and picnic area around the lake. And the location? It’s unbeatable. You’re just 5 minutes to downtown Naples, where you’ll find the beaches, world-renowned restaurants, and luxury boutiques. With no HOA fees, an incredible community feel, and a location that can’t be beaten, this home is more than just a place to live—it’s a once-in-a-lifetime opportunity.

158 Jeepers DR, Naples

Courtesy of John R Wood Properties. 239-821-9056

Selling Office: .

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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.

Lake Side Mobile Estates Real Estate & Homes