Naples · Bonita Springs · Marco Island

Naples Luxury Real Estate

Private, precise guidance for waterfront, golf, and beachfront homes across Naples and Southwest Florida.

Your Naples Real Estate Advisor

Jeremy O’Guinn is a Broker Associate and Certified Negotiation Expert with Downing-Frye Realty, representing buyers and sellers of luxury, waterfront, and golf community homes in Naples, Bonita Springs, Marco Island, and Estero, Florida, with more than 18 years of local experience.

18+Years Licensed
CNECertified Negotiator
200+Homes Sold
130+Five-Star Reviews
How Jeremy Works

A Calm, Data-First Approach to Naples Real Estate

Pricing, negotiation, and discretion for Naples buyers and sellers

01

Precision Pricing

Guidance grounded in current Naples sales, not national models that miss waterfront exposure, seasonal demand, and community dynamics in neighborhoods from Port Royal and Aqualane Shores to Pelican Bay and Vanderbilt Beach.

02

Strategic Negotiation

Calm, methodical advocacy built on the Certified Negotiation Expert framework, protecting your price, terms, and net proceeds at every stage of the transaction.

03

Discretion

Privacy-forward representation when confidentiality matters, for high-value sellers and buyers who prefer to limit public exposure while still reaching qualified buyers.

Just Listed

New Naples Listings, Updated Daily

See the newest homes for sale in Naples, sorted by listing date and pulled directly from the MLS.

Featured Communities

Naples Neighborhoods Worth Knowing

Beachfront, golf, and waterfront communities in Naples, Florida

Search by Lifestyle

Find Your Naples Lifestyle

Naples waterfront, golf, beach, estate, and gated community homes

Sunset over the Gulf of Mexico from a Naples, Florida beach
For Sellers

Selling a Luxury Home in Naples

Pricing, marketing, and negotiation for high-value Naples properties

Waterfront exposure, seasonal demand, and community-level buyer behavior move Naples values in ways national estimates miss. Every pricing recommendation starts from current local sales, reviewed personally.

The Selling Process
Meet Jeremy

Eighteen Years Advising Naples Buyers and Sellers

Broker Associate · Certified Negotiation Expert · Downing-Frye Realty

Jeremy O’Guinn has been licensed in Florida since 2008 and holds a broker’s license and the Certified Negotiation Expert designation. His practice centers on luxury, waterfront, and golf community properties from Naples to Marco Island, with a calm, data-first approach to pricing and negotiation.

  • Licensed Florida real estate broker since 2010
  • Certified Negotiation Expert (CNE)
  • Office at 8950 Fontana Del Sol Way, Naples, FL 34109
About Jeremy
Jeremy O'Guinn, Naples luxury real estate advisor and Broker Associate at Downing-Frye Realty
Client Experiences

What Clients Say About Working With Jeremy

Naples real estate reviews from buyers and sellers

“Jeremy was professional, responsive, and made the entire process feel seamless from start to finish.”
Naples BuyerSingle family home purchase
“We always felt informed and supported. Jeremy brought a calm, confident approach that made a stressful process much easier.”
Bonita Springs SellerLong-distance sale
“Jeremy was knowledgeable, strategic, and easy to work with. His communication and follow through stood out from day one.”
Pelican Bay BuyerNaples condo purchase
“Selling from out of state could have been difficult, but Jeremy handled the details beautifully and kept everything moving.”
Out-of-State SellerNaples condo sale
“Jeremy went above and beyond for our family and stayed steady even when the transaction became complicated.”
First-Time BuyerNaples home purchase
“He was prompt, courteous, and consistently professional. We felt well advised throughout the entire process.”
Mediterra BuyerLuxury home purchase
“Jeremy presented our property beautifully and used a polished, thoughtful marketing approach that gave us confidence right away.”
Naples SellerSingle family home sale
“Jeremy kept his word on communication and delivered clear advice at every stage. We always knew where things stood.”
Naples SellerSingle family home sale
“Coming from a distance, we needed someone we could trust. Jeremy helped us stay informed, focused, and confident.”
Relocating BuyerNaples condo purchase

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Questions

Naples Real Estate FAQ

Buying and selling homes in Naples and Southwest Florida

What areas does Jeremy serve?

Jeremy O’Guinn serves Naples, Bonita Springs, Marco Island, Estero, Fort Myers Beach, Sanibel, and Captiva, with a focus on luxury, waterfront, and golf community properties.

Does Jeremy represent both buyers and sellers?

Yes. Jeremy represents both buyers and sellers throughout Naples and Southwest Florida. Buyers receive objective guidance, local market insight, and careful negotiation. Sellers receive accurate pricing, strong marketing, and steady advocacy from listing through closing.

What makes Naples luxury real estate difficult to price?

Value depends on details automated tools miss: Gulf access and bridge clearance, water views, flood zone, community amenities, and seasonal demand. Pricing here starts from current local sales, not national models.

How does Jeremy market a Naples home for sale?

Every listing receives professional photography and video, targeted social media advertising, open houses, and a printed property book for buyers to take home. Condominium listings also include outreach to other owners in the building, and listings can include an interactive AI Property Companion for buyers.

Which Naples communities are best for golf?

It depends on membership style. Mediterra, Grey Oaks, Quail West, and Talis Park are private clubs with different membership structures, while communities like Pelican Marsh offer optional memberships.

Can I sell my Naples home privately?

Yes. Privacy-forward strategies can limit public exposure while still reaching qualified buyers, which suits many high-value sellers.

How does the process work when buying from out of state?

Most steps can be handled remotely, including video tours, electronic signing, and remote closing, with local inspections and walk-throughs coordinated on your behalf.

What is the best first step?

Request a confidential home value or book a 15-minute consultation to talk through timing and strategy with no obligation.

The 239 Weekly

Naples Market Insight, Every Friday

Market updates, neighborhood insight, and Southwest Florida lifestyle, delivered weekly.

New to Market in Naples

965 Tierra Lago WAY, Naples
$1,600,000
3 Beds ⋅ 4 Baths ⋅ 226039107 MLS
Tierra Lago at The Vineyards – Lake & Golf Course Views! Enjoy stunning lake and golf course views from this spacious three-bedroom plus den residence, featuring four full baths, a two-car garage, and a private pool and spa. Light and bright with desirable western exposure, the home offers a well-designed floor plan ideal for both comfortable everyday living and entertaining. The updated kitchen flows seamlessly into the main living areas, while generously sized bedrooms provide comfort and privacy. Notable updates include electric hurricane shutters, a new roof in 2021, a new A/C system in 2022, three impact-rated doors, replacement of water pressure lines in 2018, wood flooring throughout the main living areas, and a renovated primary bath. The expansive screened lanai features a pavered deck, creating an inviting outdoor retreat for entertaining, relaxing, and enjoying Naples’ beautiful sunsets against a stunning panoramic backdrop. Tierra Lago is an intimate, beautifully landscaped enclave of just 44 single-family homes within The Vineyards, one of Naples’ premier gated communities. Residents have the opportunity to enjoy the exceptional lifestyle of Vineyards Country Club, where optional membership offers access to 36 holes of championship golf, 12 Har-Tru tennis courts, pickleball, bocce, a resort-style pool and spa, and a full calendar of social activities. The impressive Wellness & Spa facility includes a fitness center, café, halotherapy salt room, massage and salon services, and a saltwater lap pool. Members can also enjoy club dining and outdoor bar service. Ideally located in the heart of Naples, The Vineyards offers convenient access to world-class beaches, upscale shopping, fine dining, and premier medical facilities. Experience a wonderful blend of scenic views, a desirable location, and the opportunity to enjoy the best of the Southwest Florida lifestyle.

965 Tierra Lago WAY, Naples

265 Indies WAY Unit 802, Naples
$2,045,000
3 Beds ⋅ 3 Baths ⋅ 226038756 MLS ⋅ Grande Geneva BLDG.
Two Horizons. One Extraordinary Address. What if your home offered two completely different worlds? Imagine a morning bathed in soft Gulf light, with the emerald greens of Old Collier Golf Course stretching toward the horizon. As the day unfolds, the waterways shimmer, the light shifts, and the pace of life seems to slow. Here, every moment feels a little more extraordinary. Welcome to a residence where every view tells a different story — the tranquil beauty of the golf course to the east and the sweeping waters of the Gulf and surrounding waterways to the west. Spanning 3,050 square feet, this exceptional high-floor residence at The Dunes was designed for those who appreciate the finer things without needing to announce them. Three bedrooms, three full baths, beautifully appointed interiors, and a wonderful sense of space create an atmosphere that feels both refined and effortlessly inviting. The primary suite is a private retreat, complete with custom closets and a spa-inspired bath. An en-suite guest bedroom offers the flexibility of a second primary suite, while thoughtful detailing, natural wood tones, and timeless craftsmanship bring warmth and understated elegance to every room. And then, there is the lifestyle. Poolside afternoons. Tennis and pickleball. Dining without leaving the community. Days spent on the water, on the golf course, or along the sugar-white sands of Vanderbilt Beach. At The Dunes, the pleasures of a resort-inspired lifestyle become part of everyday living. The anticipated Paraíso Beach Club promises to add yet another dimension to the coastal experience, further enhancing the appeal of this exceptional location. Offered turnkey and ready to enjoy, with two coveted upper-level under-building garage spaces and private storage, this is more than a place to live. It is the feeling of being on vacation, the comfort of being home, and the luxury of having both — every single day. Come experience the two horizons. You may just find your extraordinary address.

265 Indies WAY Unit 802, Naples

13915 Old Coast RD Unit 1101, Naples
$4,150,000
4 Beds ⋅ 4 Baths ⋅ 226030935 MLS ⋅ Kalea Bay Tower 100 BLDG.
TIMELESS COASTAL ELEGANCE AT KALEA BAY. Beautifully appointed and effortlessly sophisticated, this four-bedroom, four-bath residence with an additional den in Tower 100 offers a refined interpretation of luxury coastal living. A harmonious palette of crisp whites, soft neutrals, and signature coastal blues creates an inviting atmosphere, while tailored furnishings, rich textures, elegant wallcoverings, and thoughtfully selected designer accents bring warmth and character throughout. The expansive great room is designed for both gracious entertaining and relaxed everyday living, seamlessly connecting the living and dining areas with a beautifully finished open kitchen. Natural light fills the residence, highlighting the warm wood flooring and timeless architectural details. The serene owner’s suite offers a private retreat, with expansive windows framing breathtaking views across the mangrove preserve to the Gulf of Mexico and spectacular Southwest Florida sunsets. A spa-inspired owners bath and thoughtfully designed custom closet further enhance the sense of luxury. Each guest ensuite bedroom offers its own distinctive character, including elegant wallcoverings and classic coastal detailing. A standout feature is the sophisticated den, where a stunning custom wood coffered ceiling adds architectural warmth and distinction. With its rich finishes, tailored details, and abundant natural light, this versatile space is equally suited for a private office, intimate lounge, or quiet retreat with incredible east facing views of the sunrise over the Kinsale Golf course. The expansive lanai extends the home’s beautifully coordinated interiors outdoors, featuring a distinctive wood-accented feature wall, generous seating areas, and sweeping views across the lush mangrove preserve toward the Gulf. Whether enjoying morning coffee, entertaining friends, or watching the sun set over the water, this inviting outdoor living space perfectly captures the essence of the Naples lifestyle. Beyond the residence, Kalea Bay offers an extraordinary resort lifestyle with a spectacular private clubhouse, three pools, two restaurants, open-air bars, a state-of-the-art wellness center, tennis and pickleball courts, and exceptional recreational amenities. Tower 100 residents also enjoy exclusive rooftop amenities, including a pool, fitness center, and gathering spaces with panoramic views. An exceptional opportunity to experience the timeless elegance, sophisticated interiors, and unparalleled resort lifestyle that define Kalea

13915 Old Coast RD Unit 1101, Naples

6044 Plana Cays DR, Naples
$3,695,000
4 Beds ⋅ 4.5 Baths ⋅ 226039052 MLS
Once-in-a-lifetime opportunity to own a piece of paradise in one of the sought-after coastal communities in the world. Just moments from the world-renowned boutiques, restaurants, and coastal energy of downtown Fifth Avenue, and equally as close to the sugar-white sands of the Gulf, this newer construction, highly coveted Cocoplum custom residence by Stock Luxury Homes is a home designed not simply to be admired but to be experienced. From the moment you arrive a sense of quiet sophistication unfolds. Inside, nearly 3,900 air conditioned square feet of impeccably curated living space is defined by soaring custom coffered ceilings, exceptional craftsmanship, and an effortless connection between indoor elegance and the breathtaking natural beauty beyond. Walls of hurricane-impact glass frame uninterrupted lake views, transforming every room into a living portrait where shimmering water and vibrant sunsets become part of everyday life. Designed for intimate moments and unforgettable gatherings, the residence offers four spacious bedroom ensuites for maximum privacy, a versatile den or executive office/flex space, and five beautifully appointed baths. At its heart, the chef's kitchen is a masterclass in beauty and functionality, featuring gas cooking, bespoke cabinetry and exquisite finishes that inspire everything from quiet morning coffee to elegant dinner parties. Life here extends far beyond your front door. Within The Isles of Collier Preserve, a community inspired by the timeless architecture and enduring character of Old Naples, residents enjoy an exceptional lifestyle immersed in nature. More than half of its 2,400 acres have been preserved as pristine lakes, wildlife habitat and protected natural landscapes. Miles of scenic recreational, biking and kayaking trails wind through the Cypress Waterway, creating an everyday connection to Southwest Florida's remarkable beauty. At the center of the community, The Isles Club offers an amenity experience that rivals a private resort, featuring a state-of-the-art fitness center, large resort and lap pools, numerous tennis and pickleball courts, the Overlook Bar & Grill, multiple kayak launches, and miles of waterways perfect for paddle boarding, kayaking or simply embracing the peaceful rhythm of life on the water. This is more than a newly constructed luxury residence, it is an invitation to embrace one of Naples most desired lifestyles.

6044 Plana Cays DR, Naples

9653 Gulf Shore DR Unit 702, Naples
$1,749,000
2 Beds ⋅ 2.5 Baths ⋅ 226035669 MLS ⋅ Casa Grande BLDG.
Welcome to your ultimate beachfront escape at Casa Grande on Vanderbilt Beach. This stunning, fully renovated 2-bedroom, 2.5-bathroom condo offers the perfect blend of coastal elegance and modern luxury, designed to make you feel right at home the moment you step inside. The open living space is anchored by the gorgeous, top of the line Anderson natural blonde maple floors, high baseboards, and solid-core shaker doors. In the living room, a dropped light box ceiling with custom LED lighting creates a warm, inviting ambiance for relaxing after a day in the sun. If you love to entertain, you’ll appreciate the custom wet bar, complete with its own sink and wine fridge. Steps away, the chef’s kitchen is fully equipped with premium LG Studio stainless steel appliances, granite countertops, Kohler double-deep sinks, and custom solid maple cabinetry with convenient soft-close drawers and pull-outs. Grohe polished chrome fixtures and mounted TVs are featured throughout the home. The guest bedroom is incredibly versatile, featuring a custom-built Murphy bed system with integrated drawers and its own en-suite bathroom. Speaking of bathrooms, all of them have been beautifully remodeled, showcasing stunning rainfall tile and frameless glass enclosures. There is also a stylish half-bath off the main living area for guests. Thoughtful upgrades abound, including new LED lighting, a brand-new electrical panel, a newer A/C unit with a Honeywell thermostat, and Hunter Douglas remote-controlled privacy shades. For peace of mind, the condo is also equipped with new hurricane shutters. Plus, you’ll have your own separate, air-conditioned storage locker—perfect for storing your beach gear and pool toys. Living at Casa Grande puts you right in the heart of Vanderbilt Beach, just minutes from the area's top dining, shopping, and entertainment. On-site, you'll love having a private beach access, a spacious heated pool, and hassle-free guest parking right across the street. The building itself has been recently refreshed with a new roof, new exterior paint, and a new secure elevator. Plus, the community room is currently being upgraded with new furniture, a big-screen TV, and a workout nook featuring a stationary bike and elliptical. Of course, the real highlight is the breathtaking, unobstructed view of the Gulf, offering front-row seats to spectacular Florida sunsets every single night. Your paradise awaits!

9653 Gulf Shore DR Unit 702, Naples

6223 Megans Bay DR, Naples
$3,195,000
4 Beds ⋅ 4.5 Baths ⋅ 226038725 MLS
SPECTACULAR STOCK-BUILT MADISON II | 4 BEDROOMS + DEN | 5 BATHROOMS | AN OUTDOOR ENTERTAINER'S DREAM! Built in 2022 by renowned STOCK CONSTRUCTION, this exceptional residence showcases the highly sought-after MADISON II floor plan, extraordinary custom upgrades and BREATHTAKING WATER VIEWS. Rich HARDWOOD FLOORS with inlaid marble accents, CUSTOM WOOD CEILING BEAMS, plantation shutters, designer lighting and LUTRON DIMMERS create an atmosphere of coastal elegance. The great room features a stunning STACKED-STONE ACCENT WALL and illuminated shelving, while expansive CORNER SLIDING GLASS DOORS seamlessly connect indoor and outdoor living. The GOURMET KITCHEN boasts premium, appliances, custom cabinetry, decorative glass tile and enhanced island storage. The luxurious PRIMARY SUITE offers custom closets and a SPA-INSPIRED BATH with rainfall shower, body jets, premium tile and TOTO wash systems. ALL BEDROOMS FEATURE ENSUITE BATHROOMS, offering comfort and privacy for family and guests alike. The OUTDOOR LIVING SPACE is truly the showstopper! An expansive covered lanai features CUSTOM WOOD BEAMS, DESIGNER WOOD PLANK ACCENT WALL, CUSTOM WRAP AROUND CABINETRY, PANORAMIC PICTURE WINDOW SCREEN ENCLOSURE, architectural privacy walls, designer lighting and TWO-ZONED OUTDOOR AUDIO. The SPECTACULAR OUTDOOR KITCHEN includes a built-in WEBER GRILL, side burner, refrigerator, CLEAR-ICE MAKER, sink and custom wrap around cabinetry. Enjoy the HEATED SALTWATER POOL & SPA with SUN SHELF and dramatic FIRE FEATURES, surrounded by lush tropical landscaping, mature palms, PANORAMIC WATER VIEWS and NO SEE-UM SCREENS. Additional upgrades include a KOHLER WHOLE-HOME GENERATOR, 1000 GALLON PROPANE TANK, IMPACT WINDOWS AND DOORS and INTEGRATED METAL STORM SCREENS on Patio. The expansive THREE- CAR GARAGE is beautifully appointed with CUSTOM CABINETRY, offering exceptional storage and ample space for vehicles, recreational equipment, and all the essentials of an elevated Florida lifestyle. Two A/C systems, WATER FILTRATION, softening and reverse osmosis, CUSTOM LANDSCAPING including rare GREEN QUARTZITE Stone with lighting and an EXPANDED PAVER DRIVEWAY. HOME IS BEING SOLD PARTIALLY FURNISHED. Located in the 2,400-acre ISLES OF COLLIER PRESERVE, offering scenic trails, kayaking, RESORT & LAP POOLS, fitness center, 14 PICKLEBALL COURTS, tennis, bocce and the OVERLOOK BAR & GRILL. Approximately 7 MINUTES TO DOWNTOWN NAPLES, FIFTH AVENUE SOUTH and minutes to BEAUTIFUL GULF BEACHES. EXPERIENCE THE ULTIMATE NAPLES LUXURY LIFESTYLE!

6223 Megans Bay DR, Naples

16488 Felicita CT, Naples
$3,450,000
4 Beds ⋅ 5.5 Baths ⋅ 226032870 MLS
One or more photo(s) has been virtually staged, AI generated or rendered. As you step through the grand entrance of 16488 Felicita Ct, you are immediately welcomed into an atmosphere of refined elegance where soaring, volume ceilings and premium finishes set the stage for a truly luxurious living experience. This exceptional home in Mediterra invites you to explore its seamless, open-concept floor plan, beginning with a grand foyer that leads into a sophisticated living room and a tastefully appointed formal dining room that effortlessly flows toward the light filled family room and kitchen that offers a Wolf gas range with dual ovens, a Subzero refrigerator & freezer, a reverse-osmosis water filtration system, sizeable island and a walk-in pantry. In the sunlit family room beyond the zero-corner sliders, your private outdoor resort unfolds: a sprawling covered lanai boasting numerous luxury upgrades awaits. This outdoor paradise features a resurfaced pool with new fountains, fire bowls, and even a playful dolphin water feature, along with an expansive Quartz-topped bar, equipped with a Lynx gas grill, two refrigerated drawers, a mini-fridge, ice maker, Kalamazoo Artisan Fire pizza oven, Evo flat-top grill, warming drawer, new custom cabinetry & lighting fixtures. Entertain guests with ease, thanks to the ample bar and dining seating, pool bath, and a stunning see-through fireplace with multi color lighting effects and a drop-down TV. The entire outdoor experience is highlighted by new tile installation across the entire lanai deck, fireplace, pool & spa. The owner’s suite is a luxurious private retreat that opens directly to the lanai and includes a dedicated office/sitting area, two sizeable walk-in closets, dual vanities, and a spa-inspired bathroom that includes a spacious walk-in shower, a separate soaking tub overlooking an enclosed garden area and even a bonus sitting room or fitness room. The residence additionally has three en-suite bedrooms for family or guests, a large laundry room with a washer and dryer replaced in 2021, and a three-car garage. With a new 2025 roof, fresh exterior paint, a new 2025 paver driveway with front stoop/steps, and updated landscaping and sod completed in 2024-2025, this home is truly move-in ready! Mediterra is a prestigious luxury golf & country club community featuring Two championship Tom-Fazio golf courses for avid golfers, a private beach club with restaurant & bar, multiple tennis courts, pickleball & bocce, fitness center, pristine bike & jogging trails, and luxurious dining at the private country club restaurant. The Mediterra Beach Club offers an escape to a 10,000 sq. ft two-story private oceanfront paradise on the Gulf of Mexico. Featuring a restaurant & bar that serves members via indoor & outdoor dining, this private facility boasts a heated swimming pool, a sundeck, and cabana beach service for chairs, umbrellas & refreshments.

16488 Felicita CT, Naples

6075 Pelican Bay BLVD Unit 203, Naples
$899,000
2 Beds ⋅ 2.5 Baths ⋅ 226038868 MLS ⋅ Dorchester BLDG.
HOTEL-INSPIRED RETREAT AT THE DORCHESTER Experience refined coastal living in this beautifully renovated second-floor residence at The Dorchester, an intimate, concierge-style high-rise with only 86 residences in prestigious Pelican Bay. Offering approximately 1,741 square feet, this sophisticated condominium features two spacious en-suite bedrooms, two-and-a-half baths, and a light-filled, living and dining area designed for relaxed living and effortless entertaining. The serene coastal-inspired interior flows seamlessly onto an expansive private balcony overlooking the resort-style pool and lush tropical landscaping. The beautifully appointed kitchen features stainless steel appliances, granite countertops, abundant cabinetry, a walk-in pantry, and a charming breakfast area. Additional highlights include impact-resistant windows and sliding doors, a newer air-conditioning system, assigned garage parking, and a large air-conditioned storage room conveniently located just outside the residence. The Dorchester has undergone extensive renovations and offers the added benefits of a newer roof and a backup generator. Residents enjoy exceptional amenities, including attentive concierge services, guest suites, a fully equipped fitness center, a sophisticated social room with a bar and full kitchen, a resort-style pool and spa, fire pits, barbecue and picnic areas, and bicycle storage. A tram stop conveniently located behind the building provides easy access to Pelican Bay’s private beachfront, approximately one-third of a mile away, where residents enjoy beach chairs and umbrellas, beachfront dining, and miles of pristine Gulf shoreline. More than a residence, this is a sophisticated coastal sanctuary offering the privacy of a boutique building and the exceptional lifestyle of one of Naples’ most prestigious communities.

6075 Pelican Bay BLVD Unit 203, 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.

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