Charleston Square Condos for Sale in Naples, FL

2 Beds ⋅ 2 Baths ⋅ 226023484 MLS ⋅ Charleston Square BLDG.

An exceptional opportunity awaits to create your ideal North Naples retreat in this rarely available first-floor end-unit residence, tucked within the intimate enclave of Charleston Square in Imperial Golf Estates. Offering 2 bedrooms, 2 baths, and 1,643 square feet of living space, the condo provides a bright, neutral canvas ready for the next owner to infuse with their own style and vision. The desirable end-unit location enhances the sense of openness throughout the interior, while the flowing floor plan easily accommodates both seasonal and year-round living. An enclosed porch extends the living space, offering additional flexibility for a sitting area, reading nook, or year-round enjoyment. A private enclosed garage adds convenience along with valuable storage space. Charleston Square is an intimate community comprised of just 37 residences, offering a peaceful setting with beautifully maintained grounds, walking paths, and a community pool. Perfectly positioned in North Naples, the location places you just minutes from the white-sand shores of Barefoot Beach, Vanderbilt Beach, and Delnor-Wiggins Pass State Park, with Mercato, Waterside Shops, and an abundance of shopping, dining, and entertainment destinations nearby. Residents also have the option to join Imperial Golf Club, offering access to premier golf, social memberships, and an array of private club amenities. Whether you're searching for a full-time residence, seasonal getaway, or investment opportunity, this property presents an exceptional combination of location, potential, and the coveted North Naples lifestyle.

1340 Charleston Square DR Unit 101, Naples

Courtesy of Compass Florida LLC. 239-961-1170

$3,700,000

4 Beds ⋅ 4.5 Baths ⋅ 226021235 MLS ⋅ Charleston Square BLDG.

Hidden in Plain Sight on Naples’ Miracle Mile. Don’t let the street-level retail fool you. Charleston Square’s residences enjoy their own private, secured entrance, dedicated resident parking, and a lifestyle completely separate from the activity below. This beautifully updated 4-bedroom, 3.5-bath residence offers nearly 4,000 square feet of living space and lives more like a luxury home than a condominium. Freshly painted, the home feels bright, inviting, and move-in ready. Quality craftsmanship is evident throughout with oversized crown molding, substantial millwork, impact-resistant windows and doors, and timeless finishes. The culinary-inspired kitchen features Wolf and Sub-Zero appliances and premium materials designed for everyday living and entertaining. Boating enthusiasts will appreciate their new deeded dock with a 14,000-pound lift and quick access to the Gulf. Offered partially furnished, the residence also includes two assigned secure parking spaces. Residents enjoy a rooftop pool, a newly renovated social room, an updated fitness center, a brand-new roof, and one of the area’s most respected and well-managed associations. Larger dogs are welcome. Located on Naples’ coveted Miracle Mile, just across the street from the beach and moments from premier dining, shopping, and entertainment, Charleston Square offers an increasingly rare combination of privacy, space, boating access, and value. Surrounded by luxury developments commanding significantly higher prices, this hidden gem continues to surprise buyers who discover it.

1400 Gulf Shore BLVD N Unit 201, Naples

Courtesy of Compass Florida LLC. 614-562-1501

$1,650,000

3 Beds ⋅ 2 Baths ⋅ 226003065 MLS ⋅ Charleston Square BLDG.

Repositioned to Reflect Current Market Alignment : This 3BR | 2BA residence presents a rare combination of location, amenities, and long-term upside in the heart of Naples. Gulf views from two private balconies. One of only two units in the building featuring a 176 sq ft entry sitting area - adding functional square footage and meaningful differentiation. 2023 kitchen renovation with white quartz countertops, oversized island, Bosch induction cooktop, Bosch wall oven, and convection microwave. Peruvian hardwood floors throughout living areas. Split-bedroom layout. Tiled baths. 2024 high-efficiency, variable-speed HVAC with infrared air-sanitizing technology. Positioned directly next to the rooftop pool and grill and the brand-new 2025 community room with full kitchen and fitness center - an amenity advantage that supports future resale strength. Only 6 of 13 deeded boat slips currently in use. Slips may only be transferred within this 24-unit community, creating highly limited and near-certain access opportunity - a significant value differentiator in today’s Naples market. Low dues compared to competing condominiums. A recent fiber-optic internet upgrade for the whole building ensures seamless connectivity. Ground-floor retail and dining. The newly opened Four Seasons development nearby further enhances long-term positioning. Compelling price. Scarce features. Prime location.

1400 Gulf Shore BLVD N Unit 307, Naples

Courtesy of Realty One Group MVP.

$365,000

3 Beds ⋅ 2 Baths ⋅ 225082401 MLS ⋅ Charleston Square BLDG.

Located in the desirable Charleston Square neighborhood within Imperial Golf Estates, this second floor end unit condo offers comfort, style, and flexibility in one of Naples’ most established gated golf course communities. Golf membership is not required. Featuring three bedrooms, two nicely updated full baths, and a versatile flex space ideal for a den or home office, the layout is both functional and inviting. High ceilings enhance the sense of space and natural light, while all high-impact windows provide peace of mind and energy efficiency. The two bathrooms have been thoughtfully renovated, adding a fresh, modern touch. A detached one-car garage offers convenience and additional storage. Enjoy the serene lifestyle Imperial Golf Estates is known for, with beautifully maintained surroundings and close proximity to beaches, dining, shopping, and all that North Naples has to offer.

1320 Charleston Square DR Unit 201, Naples

Courtesy of John R Wood Properties.

Selling Office: John R Wood Properties.

$345,000

2 Beds ⋅ 2 Baths ⋅ 225003956 MLS ⋅ Charleston Square BLDG.

*****PRICE REDUCTION ALERT!***** BEST DEAL IN IMPERIAL GOLF ESTATES! Welcome to this charming 2-bedroom, 2-bathroom condo located in the quaint community of Charleston Square within the highly sought-after Imperial Golf Estates. This first-floor end unit offers 1,643 square feet of well-designed living space, providing the perfect blend of functionality and style. The spacious layout ensures ease of living, with plenty of natural light flooding the living space. Each bedroom is generously sized and offers ample closet space, ensuring personal comfort and privacy. The fully equipped kitchen includes essential appliances and plenty of counter space, making meal preparation a breeze. **NOTE the wallpaper in the kitchen is being removed and the kitchen/eat in kitchen is being repainted.** New pics will be uploaded upon completion. Enjoy beautiful views of the Imperial Golf Course and a preserve from the comfort of your home. The abundance of windows allows natural light to enhance the living experience. This tastefully decorated home is offered turnkey, making it move-in ready—just drop your bags and hit the links, the community pool, or head out for an evening on the town. Charleston Square is a serene, resort-like community with only 37 residences, offering amenities such as a sparkling pool and scenic walking paths—perfect for unwinding during your stay. Located just minutes from some of Southwest Florida's most beautiful beaches, as well as a plethora of amazing restaurants and shopping venues, including the vibrant Mercato, this condo combines comfort, convenience, and accessibility. This property is ideal as a winter retreat, rental property, vacation home, or year-round residence. Don't miss the opportunity to own this inviting and well-located condo in the #1 place to live in the USA, as featured in U.S. News & World Report's 2024-25 ranking. Schedule your visit today and discover what makes this condo a special place to live.

1310 Charleston Square DR Unit 101, Naples

Courtesy of Waterfront Realty Group Inc.

Selling Office: Keller Williams Marco Realty.

$392,500

2 Beds ⋅ 2 Baths ⋅ 224077579 MLS ⋅ Charleston Square BLDG.

Great inland location for this delightful, sunlit 1st floor condominium! Lush, SE golf course views within a desired N Naples gated community! A wide array of visually appealing, functional upgrades include: beautiful teak wood flooring thru main living areas, crown molding & 6" baseboards, plantation shutters, large open updated kitchen w/white extended glass paneled cabinets, counter depth refrigerator. quartz countertops, extensive tile work in updated bathrooms w/ Kohler fixtures, 2nd bedroom built-in cabinets w/ shelving, window seat & desk area, laundry LG washer/dryer plus quartz counters and cabinets, tankless water heater in addition to a Whirlpool whole home water filter system, new impact windows, interior/exterior paint, new roof & light fixtures! Front patio may be extended with privacy landscaping added for additional outdoor enjoyment! Relax around the spacious community pool and stay active with new pay-and-play tennis and pickleball courts!

1330 Charleston Square DR Unit 3-102, Naples

Courtesy of John R Wood Properties. 239-370-8879

Selling Office: Vylla Home.

$2,750,000

3 Beds ⋅ 3.5 Baths ⋅ 223051912 MLS ⋅ Charleston Square BLDG.

C11041 - Offering bucolic bay views and a superior level of amenities, this spacious great-room style unit is located in the highly coveted Charleston Square and comes with all items deemed essential to the Florida lifestyle, including a deeded boat slip and beach access across the street.

1400 Gulf Shore BLVD N Unit 211, Naples

Courtesy of John R Wood Properties. 239-777-6622

Selling Office: Premiere Plus Realty Company.

$414,000

3 Beds ⋅ 2 Baths ⋅ 223078536 MLS ⋅ Charleston Square BLDG.

What a fantastic opportunity for the most discriminating buyer!!! From the moment you enter this spotless beauty, you will be delighted at every turn. Totally renovated, and freshly painted, this home is a haven of comfort, and ready to be occupied immediately. The new Trane comfort A/C system is only 8 months old and will last for years to come. The hot water heater is one year old, and all the appliances under 2 years. Impact resistant windows were installed in 2022, and the rest of the home was professionally renovated by Tabor Construction. Everything is new, down to the freshly epoxy painted garage floor, with a new hurricane resistant garage door. Peace of mind and unparalleled beauty!!! A winning combination! Come see this one immediately, we all know it is not going to last!!!!

1335 Charleston Square DR Unit 6-101, Naples

Courtesy of Gulf Breeze Real Estate LC.

Selling Office: Premiere Plus Realty Company.

$2,600,000

3 Beds ⋅ 3 Baths ⋅ 223073904 MLS ⋅ Charleston Square BLDG.

Welcome to the pinnacle of coastal living. Discover this rare gem, a three-bedroom, three-bath just under 3,000-square-foot condominium in the boutique Charleston Square building in the highly desired Coquina Sands neighborhood. The amenities include a heated pool on the rooftop, a lounge area, billiards room with kitchen, two barbeque areas and an exercise facility. Every detail in this residence has been carefully curated to create an atmosphere of sophistication and comfort. From the deep coffered ceiling to the large open floor plan that invites you to host gatherings from your gourmet kitchen and create lasting memories. Imagine savoring the stunning gulf sunsets from the comfort of your living room. The spacious owners wing with its dual walk-in closets and the two en suite guest bedroom which offers privacy and convenience for you and your guest. This listing includes two parking spaces and a storage facility. Don't miss this opportunity to experience this coastal paradise.

1400 Gulf Shore BLVD N Unit 203, Naples

Courtesy of Premier Sotheby's Int'l Realty.

Selling Office: Caine Luxury Team.

$390,000

2 Beds ⋅ 2 Baths ⋅ 223056299 MLS ⋅ Charleston Square BLDG.

WHEN ONLY THE BEST WILL DO, Make sure you do not miss this pristine over 1,650 sq ft gulf course view condo. Offered partially furnished and with a one car detached garage. Whether for investment or a full time home, this unit pleases the eye at every turn. Updated and lovingly cared for, the kitchen has a breakfast bar, beautiful granite and newer appliances. Flooring is tile throughout with the main areas on diagonal. Beautiful crown molding and new Levelor Blinds in the main living areas. The best feature is all new impact resistant windows installed in 2022, creating safety and piece of mind. THE OUTSTANDING GEM IN THIS CONDO IS THE SOUGHT AFTER FLORIDA ROOM PROVIDING ADDITIONAL AIR CONDITIONED LIVING SPACE NOT SEEN IN MANY UNITS! This end unit with seven ceiling fans, and new smoke detectors is waiting you. COME SEE THIS BEAUTY YOU WILL NOT BE DISAPPOINTED!!!!!!

1320 Charleston Square DR Unit 2-101, Naples

Courtesy of Gulf Breeze Real Estate LC.

Selling Office: Sun Realty.

$365,000

2 Beds ⋅ 2 Baths ⋅ 223039424 MLS ⋅ Charleston Square BLDG.

Well maintained, 2nd floor Gardenia floor plan with golf course views and close proximity to the community pool. New impact windows, exterior paint and roof make this community one of the best within Imperial. New SS appliances and newer carpet and paint - just bring your finishing touches. Charleston Square is one of 13 separate associations located in Imperial. The Imperial front gate puts you minutes away from several world class beaches including Vanderbilt Beach, Barefoot Beach & Delnor-Wiggins Pass State Park and dozens of fabulous restaurants and the hottest spot in Naples - Mercato. Membership to Imperial Golf Club's (2) 18-hole championship golf courses is optional.

1310 Charleston Square DR Unit 1-202, Naples

Courtesy of Waterfront Realty Group Inc.

Selling Office: Waterfront Realty Group Inc.

$360,000

2 Beds ⋅ 2 Baths ⋅ 222067821 MLS ⋅ Charleston Square BLDG.

Spectacular!!!! this Spacious second floor unit condo with great floor plan. Upgraded kitchen, under-mount sink and faucet. This unit features vaulted ceilings, two separate dining areas as well as breakfast bar. Impressive frosted glass french doors to corner den with LOTS of New impact windows and new roof. The exterior of All 37 units has been painted , new exterior lighting. Great location in North Naples. Close to shopping, beach, hospitals and restaurants. Approximately 4 miles to Mercato/Fifth third center and 9 miles to Coconut Point Mall. Residents of Imperial Golf Estates are not required to be members of the golf course. IMPERIAL GOLF ESTATES is sought after guard gated GOLF COMMUNITY offering private and social memberships with unbelievable association fees. PRIME NORTH NAPLES LOCATION near shopping malls, grocery stores, NCH Hospital,dinning,beaches and 5 min form Mercato.

1345 Charleston Sq Dr Unit 202, Naples

Courtesy of Marzucco Real Estate.

Selling Office: Marzucco Real Estate.

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Charleston Square Condos