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

Swipe for more reviews

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

1801 Galleon DR, Naples
$45,000,000
6 Beds ⋅ 10.5 Baths ⋅ 226039870 MLS
Situated on an extraordinary lot-and-one-half in prestigious Port Royal, 1801 Galleon Drive presents a rare combination of a spectacular waterfront location, expansive grounds, and architectural elegance. Enjoying some of the most exceptional wide and long bay vistas in Port Royal, the property also offers captivating views of nature, creating an uncommon sense of privacy and tranquility. The remarkable depth of the property accommodates an impressive front motor court and courtyard while preserving an equally grand outdoor living environment. Vast terraces overlook a magnificent pool, sweeping lawns, and the breathtaking waterfront scene. A covered poolside cabana bar further enhances the home's luxurious entertaining capabilities. Encompassing approximately 13,775 square feet under air, the beautifully appointed residence embodies a timeless, traditional architectural aesthetic with an enduring sense of sophistication and refinement. Elegant formal living and dining rooms feature extensive custom millwork, while two separate offices, a spacious family room, multiple casual dining areas, a theater, and a large flex space above the garage provide notable versatility. The main residence currently offers six bedrooms with additional private guest quarters above the north garage with a generously proportioned bedroom, bathroom, and dedicated living area. Four garage bays provide appeal for the automotive enthusiast, further enhancing the property's stately amenities. With its panoramic waterfront setting, verdant grounds, distinguished architectural character, and outstanding spaces for entertaining family and friends, 1801 Galleon Drive represents a truly distinctive Port Royal offering. Eligibility for Port Royal Club membership adds to the property’s appeal with the opening of the newly completed Port Royal beach club.

1801 Galleon DR, Naples

10475 GULF SHORE DR Unit 132, Naples
$1,199,000
2 Beds ⋅ 2 Baths ⋅ 226040274 MLS ⋅ Bayshores BLDG.
Experience the rare privilege of living directly on the sands of Vanderbilt Beach, where the Gulf of Mexico becomes an extension of your own backyard. Situated within Bayshores of Vanderbilt Beach, an intimate beachfront enclave of just 30 residences, this beautifully renovated two-bedroom, two-bath condominium offers an exceptional combination of coastal tranquility, breathtaking scenery and investment potential. Sweeping Gulf views, swaying palms and spectacular sunsets create an unforgettable setting, while the gentle sounds of the surf provide a soothing backdrop from the Gulf-facing primary suite. Thoughtfully updated, the residence features an inviting open living and dining area, in-unit laundry, high-speed Wi-Fi and a spacious primary suite with a dressing area and walk-in closet. The guest bedroom enjoys picturesque views of Wiggins Pass Lagoon and the community's tennis and pickleball courts. Screened in Lanai overlooking the Gulf for your perfect backdrop for morning coffee, afternoon relaxation, or sunset evenings. Just steps from your door, discover an idyllic stretch of beachfront, a heated Gulf-front swimming pool and lush tropical grounds that enhance the property's peaceful, private atmosphere. Additional conveniences include a private Cabana, assigned parking space near the building, guest parking and the opportunity to rent or purchase boat dockage. Enjoy leisurely beachfront walks, dolphin and manatee sightings, and sunset evenings along the shoreline, with the acclaimed beachfront dining at Baleen at LaPlaya Beach & Golf Resort just a short stroll away. Beyond its extraordinary lifestyle appeal, this residence offers outstanding flexibility for owners and investors alike. The community's desirable rental policy permits a minimum stay of 14 nights and up to 26 leases annually, complemented by the property's established rental history. The building has also completed its Milestone Inspection and Structural Integrity Reserve Study. Whether envisioned as a personal waterfront retreat, seasonal escape or income-producing investment, this exceptional Gulf-front residence captures the essence of effortless Naples beachfront living.

10475 GULF SHORE DR Unit 132, Naples

14516 MARSALA WAY, Naples
$2,725,000
3 Beds ⋅ 4 Baths ⋅ 226040151 MLS
An exceptional expression of contemporary luxury awaits within Marsala at Tiburón, an intimate, gated enclave of just 56 residences nestled within the prestigious Tiburón Ritz-Carlton Golf Resort community. Distinctive architectural details, sophisticated design and an effortless connection between indoor and outdoor spaces define this remarkable custom residence. An expansive, light-filled floor plan encompasses three bedrooms plus a den, with walls of glass framing captivating golf course vistas and the shimmering pool beyond. The primary retreat offers a serene escape, complete with a beautifully appointed contemporary bath and spacious walk-in closet with beautiful custom cabinetry, while a spacious guest suite provides exceptional privacy with its own ensuite bath and walk-in closet. Designed for the quintessential Naples lifestyle, the expansive lanai and natural stone pool terrace create an inviting setting for alfresco entertaining, quiet relaxation and enjoying the picturesque surroundings. Other special features include; reverse osmosis, water softener, whole house generator, 3 newer AC units, newer pool cage with panoramic screen supports up to 190 mph winds, newer pool equipment, storm smart storm screens for the lanai, and an oversized air conditioned three-car garage with epoxy floor. This extraordinary offering, where architectural individuality meets the elegance and luxury of one of Tiburón's most special residential enclaves. FULL GOLF & SOCIAL MEMBERSHIPS ARE IMMEDIATELY AVAILABLE, but not required to live in the community. Tiburón golf members enjoy 36 holes of Greg Norman–designed championship golf, dining, fitness, spa and tennis facilities, concierge services, and a private beach shuttle. The home is located just 3.5 miles from Vanderbilt Beach and about 1.5 miles from shopping and dining at Mercato.

14516 MARSALA WAY, Naples

632 HICKORY RD, Naples
$13,995,000
6 Beds ⋅ 9.5 Baths ⋅ 226038750 MLS
WELCOME TO YOUR OWN PRIVATE PARADISE! Discover a rare opportunity to own a breathtaking, newly built luxury estate on 1.76 acres in the highly sought-after Pine Ridge community of Naples. Behind two elegant electric gates, a world of beauty, privacy, and resort-style living awaits. Lush tropical gardens, exotic plants, and towering privacy walls create a peaceful retreat unlike any other. From the moment you enter, prepare to be amazed! Your eyes are drawn through the grand living space to a spectacular resort-style pool and beautiful guest house beyond. This stunning first impression sets the stage for an estate designed to impress at every turn. LIVE EVERY DAY LIKE YOU'RE ON VACATION! At the heart of this private oasis is a magnificent 75-by-20-foot pool with a sun shelf, spa, and fountain. Swim laps, soak up the Florida sunshine, or unwind beneath the umbrellas. Gather around the large fire pit, entertain at the outdoor summer kitchen, or enjoy quiet evenings on the covered, screened lanais. A cold plunge and hot sauna bring the luxury spa experience right to your doorstep. SPACE TOGETHER. PRIVACY APART. The grand main residence offers five ensuite bedrooms, spacious living areas, upstairs bonus room, and soaring vaulted ceilings with rich wood accents. A separate guest house with a bedroom, flexible bonus room, and two full baths provides a wonderful private retreat for family and friends. Whether hosting weekend guests, welcoming extended family, or creating a peaceful home office, this estate offers the freedom to live your way. DESIGNED TO INSPIRE. BUILT TO IMPRESS. Created by KKG Builder Developer, this exceptional home blends striking design with everyday comfort. The stunning great room flows into a gourmet kitchen featuring glowing Cristallo quartzite, a six-burner Wolf gas range, Sub-Zero refrigerator, and Bosch dishwasher, and so much more. A spacious butler's pantry with service doors makes entertaining effortless. Two gas fireplaces add warmth and charm, while three laundry rooms bring added ease to daily life. An oversized four-car garage with room for future vehicle lifts, a whole-house Generac generator, and carefully planned systems add comfort and peace of mind. RARE PRIVACY. REMARKABLE BEAUTY. ENDLESS POSSIBILITIES. More than a luxury home, 632 Hickory Road is a private world of its own. A place to celebrate, recharge, welcome loved ones, and create lasting memories. With extraordinary outdoor living, stunning new construction, and the space to enjoy it all, this Pine Ridge estate offers a lifestyle that is truly hard to find. EXPERIENCE THE EXTRAORDINARY. YOUR PRIVATE NAPLES PARADISE AWAITS!

632 HICKORY RD, Naples

3205 Kumamoto LN, Naples
$2,695,000
3 Beds ⋅ 3.5 Baths ⋅ 226039645 MLS
Excellent opportunity to secure this RARELY available and first time on the market Iris model in Oyster Harbor, completed in 2023 by Gulf Bay Homes & MHK Architecture. From the minute you enter you feel the warmth of this CUSTOM ,TAILORED ,ELEVATED and CHIC home. The IRIS popular layout allows for those that desire privacy and elegance.This truly spectacular 3 bedroom, 3 1/2 bath plus a den/ home office or 4th smaller bedroom floorpan boosts 3426 square ft under air and a total of 4518 sq ft livable luxury. From its inviting interiors and beautifully appointed living spaces to its seamless indoor-outdoor lifestyle, every detail reflects the best selection of material to make this home one of a kind. Expansive upgrades and details are noticed immediately throughout the entire residence. Light wood flooring, coffered ceilings, custom trim work, Sonos speaker living room, a butlers pantry, quartz countertops, custom designer wall coverings, an oversized walk-in primary closet, sitting area/office in primary , a 43" linear 2 way gas fire place, oversized storage closets, designer choice lighting fixtures, alarm system, and custom stonework. Open concept living allows complete integration to your private pool/spa oasis, a fully appointed outdoor kitchen with stainless steel appliances, a gas grill, outdoor under cover dining and entertaining area, private courtyard with artificial grass decor wall, a heated salt water pool/spa with autofill, tankless water heater, impact resistant windows and doors, electric hurricane shutters lanai, motorized retractable screens, peace of mind knowing this home is private, quiet, and secure. Residents can expect to enjoy a resort lifestyle with miles of tree lined scenic walkways, pickleball, tennis, fitness center and spa, fine dining and resort style pools. Nestled within the prestigious Fiddlers Creek Community in Naples, FL this exceptional home offers a lifestyle designed by resort amenities, natural beauty, and effortless elegance. Best of all just a short drive to Southwest Florida's finest white sandy beaches, restaurants galore, boutique shopping and so much more.

3205 Kumamoto LN, Naples

4091 29th AVE NE, Naples
$950,000
6 Beds ⋅ 4 Baths ⋅ 226040243 MLS
THREE HOMES, ONE INCREDIBLE PROPERTY — A RARE OPPORTUNITY IN NAPLES, FLORIDA! Imagine owning not one, not two, but THREE beautiful residences on one spectacular 1.59-acre property! Welcome to a truly exceptional property in Naples, Florida, where space, privacy, comfort, and endless possibilities come together! THREE SEPARATE RESIDENCES , 8 BEDROOMS & 4 BATHROOMS IN TOTAL! RESIDENCE #1 — MAIN HOME,3 spacious bedrooms,2 full bathrooms,Fully equipped kitchen,Private outdoor terrace,Dedicated laundry area RESIDENCE #2 — SECOND HOME,3 comfortable bedrooms,1 full bathroom,Fully equipped kitchen,Private outdoor terrace,Dedicated laundry area RESIDENCE #3 — GUEST HOUSE,2 bedrooms,1 full bathroom,Private kitchen,Outdoor terrace. AND THAT'S JUST THE BEGINNING! This incredible property sits on 1.59 ACRES OF LAND, featuring: Fully paved grounds, Completely fenced property, Installed entrance gate for added privacy,Large, fully insulated warehouse-style building, Three independent residences, Three kitchens and Private outdoor terraces Plenty of space, flexibility, and possibilities ONE PROPERTY…… THREE HOMES. ENDLESS OPPORTUNITIES! Whether you're looking for a multigenerational family compound, a private retreat, or a property with potential rental income, this unique opportunity offers an extraordinary combination of versatility and privacy. Imagine having your family close while everyone enjoys their own independent living space. Or picture the possibilities of owning three residences on one expansive property in desirable Naples, Florida!

4091 29th AVE NE, 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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