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

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 with a relaxed tropical aesthetic, 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. 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 an 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

880 8th AVE S Unit 202, Naples
$1,295,000
3 Beds ⋅ 2 Baths ⋅ 226040116 MLS ⋅ Gloucester Bay 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 AVE S Unit 202, Naples

9150 Torrefino CT, Naples
$2,400,000
4 Beds ⋅ 3.5 Baths ⋅ 226039800 MLS
Experience exceptional indoor-outdoor living in this beautifully maintained and extensively updated courtyard residence, featuring a three-bedroom, two-and-a-half-bath main home and a private one-bedroom, one-bath guest casita. Designed around a spectacular tropical courtyard, this residence offers the perfect combination of privacy, comfort and effortless entertaining. The stunning outdoor living area is the centerpiece of the home, featuring a sparkling saltwater pool, raised spa, expansive natural stone decking and lush tropical landscaping. Multiple covered seating and dining areas provide inviting spaces to relax or entertain, while professionally installed landscape lighting transforms the courtyard into a beautiful evening retreat. The separate guest casita offers privacy and flexibility for visiting family and friends. Inside, soaring ceilings, abundant natural light and an open, flowing floor plan complement approximately $125,000 in interior and courtyard improvements. Updates include $60,000 in flooring throughout, $35,000 in natural stone courtyard pavers and pool coping, and $20,000 in kitchen enhancements. The spacious kitchen features beautiful updated countertops and backsplash, an induction cooktop, updated sink, generous cabinetry and breakfast bar seating. The primary suite offers a spacious bathroom with a soaking tub beneath an elegant arched window, dual vanities with updated countertops and fixtures, and a separate shower. Additional improvements include updated powder room finishes, replaced air conditioning systems and pool heater, a saltwater pool conversion, new courtyard awnings and a recently installed garage door opener. The exterior was freshly painted in 2025. Meticulously cared for and thoughtfully improved, this exceptional residence offers a private tropical sanctuary with flexible guest accommodations and beautifully appointed indoor and outdoor living spaces. A wonderful opportunity to enjoy the Naples lifestyle.

9150 Torrefino CT, Naples

37 Johnnycake DR, Naples
$1,049,000
3 Beds ⋅ 2 Baths ⋅ 226040023 MLS
NON-FLOOD ZONE POOL HOME UNDER 4 MILES TO THE BEACH — AND NOTHING TO DO BUT UNPACK! This GULFSTREAM HOMES “HAMPTON” MODEL in CHATHAM WOODS, one of the NEWER ENCLAVES within WILLOUGHBY ACRES, has been METICULOUSLY MAINTAINED with nothing deferred. Offering 3 BEDROOMS + DEN/4TH BEDROOM and 2 BATHS across 2,280 SQ FT, the home sits on a FULLY FENCED 0.23-ACRE LOT wrapped in LUSH LANDSCAPING for EXCEPTIONAL PRIVACY. Step outside to your own BACKYARD RESORT: a PRIVATE POOL with SUN SHELF, a CUSTOM OUTDOOR KITCHEN, and a lanai with MOTORIZED HURRICANE SHUTTERS ON ALL OPENINGS, ALONG WITH BUG SCREENS. IMPACT-RESISTANT FRONT WINDOWS & DOORS. The HVAC is SERVICED TWICE A YEAR, and recent updates include a NEW MICROWAVE & PRIMARY BATH VANITY LIGHTING (2026); NEW DISHWASHER, POOL PUMP & PRIMARY BATH FAUCETS (2025); and a NEW REFRIGERATOR (2023). Inside, an OPEN FLORIDA-LIVING LAYOUT features VAULTED and TRAY CEILINGS, a welcoming foyer, pantry, built-in cabinetry, fresh interior paint, custom window treatments, upgraded cabinet hardware, DUAL WALK-IN CLOSETS in the primary suite, and OVERHEAD STORAGE in the 2-CAR GARAGE. LOW HOA fees INCLUDE LANDSCAPING & IRRIGATION MAINTENANCE, NO PET APPROVAL is needed, and the non-gated community offers BIKE & JOG PATHS and UNDERGROUND UTILITIES. UNBEATABLE NORTH NAPLES LOCATION: minutes to MERCATO, WATERSIDE SHOPS, ARTIS—NAPLES, world-class golf and dining, and DOWNTOWN NAPLES, with Aubrey Rogers High School and North Naples Middle School close by.

37 Johnnycake DR, Naples

5960 Bur Oaks LN, Naples
$1,299,000
3 Beds ⋅ 2 Baths ⋅ 226039998 MLS
A Rare Find - Space, Privacy, Freedom & an Exceptional Location! Welcome to a truly special property offering the perfect combination of style, space, and location. Situated on an impressive 1.14-acre homesite in the highly sought-after neighborhood of Oakes Estates! This beautiful renovated 3-bedroom + den residence offers something increasingly hard to find: room to spread out, privacy, and NO HOA or deed restrictions! From the moment you arrive, the property makes a statement with its beautiful automatic entry gate, creating an impressive sense of arrival and added privacy. Inside, you'll find a completely renovated home filled with natural light, a bright and inviting atmosphere, and thoughtfully updated finished throughout. Big-ticket improvements include a newer roof and new AC system, while fresh landscaping adds to the home's incredible curb appeal. And the possibilities outside are just as exciting! With 1.14 acres, there's plenty of room to create your dream backyard oasis, add a pool, build a guest house, or simply enjoy the freedom and space that comes with owning a property of this size. Location is another major highlight! Enjoy the convenience of being within a mile of Target, I-75, shopping, dining, and the pristine Gulf beaches - all while coming home to the space and privacy of an established, highly desirable neighborhood. Properties offering this much land, this level of renovation, this location, and the freedom of no HOA is truly hard to come by. Enjoy the 3D Virtual Tour! Don't miss the opportunity to make this exceptional property your own!

5960 Bur Oaks LN, 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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