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33 3rd S St, Naples
$5,500,000
4 Beds ⋅ 3.5 Baths ⋅ 226040276 MLS ⋅ Olde Naples BLDG.
British Cayman–inspired architecture, fresh interiors, and a coveted Old Naples location come together at this beautifully remodeled, fully furnished residence. Just three blocks from the Gulf beaches and five blocks north of Fifth Avenue South, the home places shopping, dining, and days by the water within easy reach. The property remained free of water intrusion during both Hurricanes Ian and Milton. Set behind lush landscaping and a circular paver driveway, custom mahogany doors open to a spacious great room with views across the pool and tropical terrace. French oak flooring, a soft neutral palette, and carefully selected designer finishes bring warmth and continuity throughout the two-story layout, which includes four bedrooms, three full baths, and two half baths. The main-level primary suite features two walk-in closets and a beautifully appointed bath. A generous kitchen with premium appliances and a gas cooktop provides plenty of space to prepare meals and gather, while the outdoor kitchen makes alfresco entertaining equally inviting. Andersen impact windows and doors add to the home’s thoughtful appointments. Outside, the private heated pool and spa anchor a lush retreat with room for lounging, dining, and hosting friends. From quiet mornings on the terrace to beach afternoons and evenings on Fifth Avenue South, this home offers an effortless way to enjoy the Old Naples lifestyle.

33 3rd S St, Naples

880 8th S Ave Unit 202, Naples
$1,295,000
3 Beds ⋅ 2 Baths ⋅ 226040116 MLS ⋅ Olde Naples BLDG.
Welcome to Gloucester Bay! This beautifully updated & exceptionally spacious 3-bedroom, 2-bathroom end-unit residence offers one of the largest floor plans available in downtown Naples at this price point! Featuring 3 full bedrooms, generous living areas, & an expansive, open floor plan, this remarkable condo delivers an incredible combination of space, location, privacy, & value. Currently the lowest-priced 3-bedroom condominium available in downtown Naples, this is a rare opportunity to enjoy the comfort & space of a move-in-ready single-family home just steps from Fifth Avenue South & Cambier Park. From the moment you enter, you'll appreciate soaring vaulted ceilings, abundant natural light, & oversized rooms that create a bright, open, inviting atmosphere. Unlike many downtown condos w/ confined layouts, this residence offers exceptional space & flexibility w/ the convenience of low-maintenance condominium living. Plantation shutters, crown molding, tasteful updates, & custom finishes add warmth & character throughout. The spacious kitchen features granite countertops, stainless steel appliances, & generous cabinetry. Expansive living & dining areas flow into an enclosed, air-conditioned Florida room, providing additional comfortable living space year-round. Step outside onto your large covered private deck overlooking the sparkling association pool & lush tropical landscaping, ideal for morning coffee or evening cocktails. Gloucester Bay is an intimate, low-density community of just six residences, offering privacy & tranquility rarely found this close to downtown. Beautifully maintained grounds feature mature tropical landscaping & a heated association pool w/ a recently installed heater. Another notable advantage is the property's elevated setting, w/ the community reporting no hurricane damage to its residences during the last three major storms. The location is exceptional! Just steps from your front door, enjoy the boutiques, acclaimed restaurants, galleries, & entertainment of Fifth Avenue South. Just a block away, Cambier Park offers tennis courts, playgrounds, green space, & the Norris Center. A nearby public boat launch provides access to Naples Bay, while Naples' world-famous white sandy beaches & breathtaking Gulf sunsets are a short bike ride away. Additional features include covered parking, ample guest parking, dedicated in-unit laundry, abundant storage, & a newer roof. The property also offers flexibility for seasonal use & investment opportunities. Three full bedrooms, expansive living space, an unbeatable downtown location, & exceptional value. Whether you're searching for a full-time residence, seasonal retreat, or investment property, this Gloucester Bay condominium offers a rare opportunity to enjoy the best of the Naples. One or more photos have been virtually staged, AI-generated, or rendered.

880 8th S Ave Unit 202, Naples

995 9th S Ave Unit 4, Naples
$1,274,900
2 Beds ⋅ 2.5 Baths ⋅ 226038264 MLS ⋅ Olde Naples BLDG.
Rare opportunity to own a fully renovated, luxurious townhome in the heart of downtown Naples at an incredible value. Ideally located in the exclusive Naples Marina Villas, this residence offers a truly walkable lifestyle just steps from the Naples Boat Club, Tin City, Fifth Avenue South, Cambier Park, waterfront dining, boutique shopping, art galleries, marinas, and everything that makes downtown Naples one of the most desirable destinations in Florida. Opportunities to enjoy this level of convenience, lifestyle, and proximity to Naples' most coveted attractions at this price point are exceptionally rare. This spacious residence features two oversized primary suites, a spacious first floor den that can be used as a dedicated workspace/office or third bedroom, floor-to-ceiling impact glass, and four private balconies, perfect for enjoying Naples' year-round sunshine. A fully renovated up and upgraded kitchen features ample soft-close cabinetry, matching GE appliances and quartz counters with a waterfall edge. A private attached two-car garage is a highly sought-after and uncommon feature in Olde Naples, along with additional private and guest parking, which provides convenience rarely found in downtown living. The pet-friendly property also includes plenty of outdoor yard space, a new washer and dryer on the first floor, new HVAC and water heater as well as a newer roof on the building. Nestled within a quiet boutique community of only six residences, this impeccably maintained home offers the perfect combination of privacy and walkability. For investors, the property boasts a strong rental history and exceptional income-producing potential, allowing for both seasonal and long-term leasing opportunities. Memberships to the marina across the street for boat slip and pool access add even more lifestyle value. Whether you're seeking a full-time residence, the perfect seasonal retreat, or an investment property with strong income history, this downtown Naples gem delivers unmatched value, location, and flexibility.

995 9th S Ave Unit 4, Naples

995 9th S Ave Unit 5, Naples
$1,350,000
3 Beds ⋅ 2.5 Baths ⋅ 226035932 MLS ⋅ Olde Naples BLDG.
One or more photo(s) has been virtually staged, AI generated or rendered. Experience the best of downtown Naples living in this beautifully updated three-story townhouse villa, ideally located just moments from 5th Avenue South, Tin City, the Naples Marina, and the Cambier Park Tennis facility. Don't forget The Avenue that is under construction which will offer 75,000 sqft of retail and dining options. Offering 1,395 square feet of thoughtfully designed living space, this residence features three bedrooms plus a den, two full baths and 1 half bathroom, and the highly desirable convenience of a rare two-car garage. Filled with natural light, the home blends timeless character with modern updates. A beautifully renovated kitchen and updated baths complement the rich Opus hardwood flooring throughout the main living areas, tile in the baths, and durable vinyl flooring on the garage level. Hurricane-rated windows and doors provide added peace of mind, while generous pet and rental policies offer flexibility for both full-time residents and investors. Enjoy the convenience of being close to Naples' renowned dining, shopping, waterfront, parks, tennis, and entertainment—all without sacrificing the space and functionality of a true three-level home.

995 9th S Ave Unit 5, Naples

250 S Golf Dr, Naples
$5,300,000
3 Beds ⋅ 4 Baths ⋅ 226033993 MLS ⋅ Olde Naples BLDG.
One or more photo(s) has been virtually staged, AI generated or rendered. A rare Old Naples opportunity offering 0.35 acres and 96 feet of frontage, just a short walk to the beach and the newly completed Four Seasons Resort. Adding to its appeal, the property fronts the Four Seasons golf course, providing an open outlook and no residence directly across the street. MHK Architecture has prepared a report identifying an 8,427-square-foot buildable area and 5,422-square-foot allowable footprint, presenting an exceptional opportunity to create a substantial custom estate in one of Naples’ most coveted locations. The existing 3,016-square-foot residence offers 3 bedrooms plus a den/office, 4 baths, a private pool and spa, and a well-appointed kitchen. Significant improvements completed in 2023 include a new roof, pool heater, HVAC system, water heater, refrigerator and dishwasher, new carpet throughout, kitchen and guest bathroom countertops, and a new guest bathroom off the den. Whether envisioned as a sophisticated renovation or replaced with a new custom residence, this exceptional homesite offers possibilities rarely found in Old Naples. The Gulf beaches and Four Seasons are a short walk away, while 5th Avenue South and 3rd Street South are approximately five minutes by car, placing Naples’ finest dining, boutique shopping, galleries, and downtown amenities within easy reach. Rare land. Exceptional frontage. An open outlook across the Four Seasons golf course. And one of the most coveted locations in Old Naples.

250 S Golf Dr, Naples

415 10th S Ave Unit 7, Naples
$1,075,000
2 Beds ⋅ 2 Baths ⋅ 226031472 MLS ⋅ Olde Naples BLDG.
Exceptional Opportunity in the Heart of Old Naples. Rare opportunity to own a garage condominium just four blocks to the beach in the heart of Old Naples. Located in an intimate eight-residence building, this second-floor two-bedroom, two-bath residence offers privacy, natural light, and exceptional walkability to 5th Avenue South and 3rd Street South. The home features two south-facing screened lanais, and a detached one-car garage — a rare amenity in this price range. Concrete block construction, high-and-dry positioning through recent storms, and a well-maintained community with pool enhanced long-term value and peace of mind. Offered in original condition, the residence presents a compelling opportunity to renovate and personalize in one of Naples’ most sought-after neighborhoods. Ideal as a seasonal retreat, investment property, or full-time coastal residence. An undervalued, garage-equipped Old Naples entry with potential renovation upside.

415 10th S Ave Unit 7, Naples

40 5th S Ave, Naples
$12,500,000
5 Beds ⋅ 6.5 Baths ⋅ 226029919 MLS ⋅ Olde Naples BLDG.
GULF AND FIFTH AVENUE IS AT YOUR FRONT DOOR… EXQUISITE CURB APPEAL with circular drive way, magnificent royal Palms trees boarder the entire estate. Wrought-iron power gates, and twin limestone staircases to front door. As you enter twenty-four-foot foyer. Mediterranean in spirit, furnished, ready to live. First floor: fireplace living room to an eight-hundred-bottle wine room, family room to a Gulf-glimpse terrace, rotunda dining for ten, ground-floor primary with pool terrace, private elevator to every level. Upstairs: parlor and bar, office, ensuite(4) guest quarters, roof top deck. Resort pool and spa on an 85’X 150’ beach-block lot, three-car alley garage. Walk to the beach, dinner, galleries, Cambier Park. For a family, a host, or a second-home buyer who wants the Gulf and downtown in one address. Come see this home at the Golden hour.

40 5th S Ave, Naples

365 5th S Ave Unit 307, 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 S Ave Unit 307, Naples

292 14th S Ave Unit A, Naples
$2,499,000
3 Beds ⋅ 3 Baths ⋅ 226010662 MLS ⋅ Olde Naples BLDG.
A rare opportunity in the heart of Olde Naples. Originally two residences, Units A & B have been masterfully combined into the only 3-bedroom residence in Petit Square, offering 2,038 square feet, 3 full baths, two covered carports, elevator access, and beautiful city views. Completely renovated with high-end finishes, the residence features elegant Carrara marble flooring, Mystery White marble countertops, a chef’s kitchen with premium stainless-steel appliances, formal dining, eat-in kitchen, and bar seating. The thoughtful single-level layout offers exceptional space, quality, and style. Recently, a smaller 1,166-square-foot unit in the building sold for $1,325,000 ($1,140/SF), making this substantially larger, fully renovated residence an exceptional value at just $1,226/SF. Petit Square offers a charming courtyard with mature trees and fountain and is pet-friendly. Ideally located just steps from Third Street South and only two blocks to the beach, with restaurants, boutiques, galleries, and the Gulf all within easy walking distance. A truly rare combination of size, renovation, parking, location, and walkability in Olde Naples.

292 14th S Ave Unit A, Naples

1160 8th S St, Naples
$4,950,000
6 Beds ⋅ 4.5 Baths ⋅ 225064774 MLS ⋅ Olde Naples BLDG.
One or more photo(s) has been virtually staged, AI generated or rendered. Price significantly reduced and now priced to sell. Offering nearly 6,000 square feet of luxurious living space, this exceptional Olde Naples residence features 6 bedrooms, 4.5 bathrooms, a private den, library, and an impressive third-floor bonus room ideal for entertaining, a media room, game room, or private retreat. Designed for both everyday living and grand-scale entertaining, the gourmet kitchen is a chef's dream, appointed with Sub-Zero and Wolf appliances, dual dishwashers, and an oversized walk in pantry. A dramatic two story foyer, illuminated by an imported chandelier, welcomes you inside and leads to an elegant second floor mezzanine, complemented by a grand staircase and solid mahogany doors throughout. The private backyard oasis features a heated saltwater pool with a tranquil water feature, surrounded by lush tropical landscaping and mature trees for exceptional privacy. From the expansive third floor terrace, enjoy spectacular bird's eye views while watching the City of Naples Fourth of July fireworks, an unforgettable experience from the comfort of your own home. Perfectly positioned in the heart of Olde Naples, this fully remodeled residence is just a short walk to world-class beaches, renowned dining, boutique shopping, and boating. Additional highlights include garage ceiling height designed to accommodate a future vehicle lift, plus multiple flexible living spaces including an exercise room, family room, media room, and bonus room to suit a variety of lifestyles. This is an exceptional opportunity to own one of Olde Naples' largest and most versatile homes at an outstanding value. Combining remarkable size, luxury finishes, and an unbeatable location, this move-in-ready residence is priced to attract immediate interest. Don't miss this rare opportunity, A must see!

1160 8th S St, Naples

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