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

111 1st ST, Naples
$1,280,000
4 Beds ⋅ 3 Baths ⋅ 226036915 MLS
**EXCEPTIONAL LUXURY, STUNNING DESIGN & THE ULTIMATE FLORIDA LIFESTYLE! NO HOA FFES** Welcome to this BREATHTAKING, nearly NEW 2024-built residence in the desirable Trail Acres community of Naples! Situated on an OVERSIZED CORNER LOT, this extraordinary 4-BEDROOM PLUS DEN, 3-FULL-BATH home offers approximately 3,500 square feet of beautifully designed living space, a spectacular HEATED SALTWATER POOL, EXPANSIVE SCREENED LANAI, FULL OUTDOOR KITCHEN, and an impressive CIRCULAR PAVER DRIVEWAY. Every detail has been thoughtfully designed to deliver sophistication, comfort, and effortless indoor-outdoor living. Ideally located just south of US-41, enjoy convenient access to Marco Island, Downtown Naples, world-famous Gulf beaches, shopping, dining, and entertainment. From the moment you arrive, the home's striking curb appeal, lush landscaping, expansive driveway, and elegant double-door entrance create an unforgettable first impression. Step inside to discover a grand foyer, SOARING CEILINGS, exquisite finishes, custom lighting, and beautiful tile flooring throughout. Expansive floor-to-ceiling glass doors flood the interior with natural light while creating a seamless connection to the spectacular outdoor living areas. At the heart of the home, the GOURMET KITCHEN is a true showpiece, featuring gorgeous QUARTZ COUNTERTOPS, premium stainless steel appliances, cooktop, DOUBLE WALL OVENS, generous cabinetry, pantry, WET BAR, and dedicated WINE REFRIGERATOR. The spacious living and dining areas flow effortlessly together, creating an exceptional setting for both everyday enjoyment and unforgettable entertaining. Step outside and experience your very own PRIVATE RESORT-STYLE PARADISE! The enormous screened lanai showcases a magnificent HEATED SALTWATER POOL, an expansive covered entertaining area with a CUSTOM WOOD-PLANK CEILING, and a fully equipped OUTDOOR PROPANE KITCHEN WITH SINK—perfect for hosting family and friends year-round. The luxurious PRIMARY SUITE offers private lanai access, spacious walk-in closets, dual vanities, a relaxing SOAKING TUB, and an impressive MULTI-HEAD WALK-IN SHOWER. A thoughtfully designed split-bedroom floor plan provides privacy and comfort, including a guest ensuite with convenient lanai access and generously sized additional bedrooms. The versatile DEN is ideal for a private home office, study, or additional flex space. Additional premium features include HURRICANE-IMPACT WINDOWS AND DOORS, a WHOLE-HOME GENERAC PROPANE GENERATOR, beautifully landscaped grounds, an EPOXY-FINISHED TWO-CAR GARAGE, and abundant driveway parking. With nearly every major component dating to 2024, this exceptional property offers the benefits of modern construction and the peace of mind today's buyers desire. **A RARE OPPORTUNITY TO OWN A NEARLY NEW NAPLES LUXURY HOME WHERE ELEGANT INTERIORS, SPECTACULAR OUTDOOR ENTERTAINING, AND AN OUTSTANDING LOCATION COME TOGETHER!** Experience the very best of Southwest Florida living!

111 1st ST, Naples

1135 3rd AVE S Unit 318, Naples
$1,895,000
2 Beds ⋅ 2.5 Baths ⋅ 226037801 MLS ⋅ Naples Square BLDG.
One or more photo(s) has been virtually staged, AI generated or rendered. One or more photo(s) has been virtually staged, AI generated or rendered. Sophisticated Coastal Living in the Heart of Downtown Naples! Discover the perfect blend of luxury, comfort, and convenience in this beautifully appointed residence in highly desirable Naples Square III. Filled with natural light and thoughtfully designed, this exceptional home offers two spacious bedrooms, two full baths, a powder room, and a versatile den, ideal for a home office or additional gathering space. Elegant white tile flooring throughout creates a bright, contemporary feel, complemented by an impressive collection of upgrades, including custom built-in cabinetry in the den and great room, designer lighting, motorized window shades, and distinctive finishes. The beautifully equipped gourmet kitchen features stylish cabinetry, a custom backsplash, electric cooktop with the option to convert to natural gas, vent hood, and double wall ovens—perfect for both casual meals and entertaining. Expansive sliding glass doors open to a generous west-facing lanai overlooking the lushly landscaped courtyard, providing an inviting extension of the living space. Enjoy warm afternoon sunshine, beautiful sunset skies, and tranquil views in this private outdoor retreat. Naples Square III offers an exceptional resort-style lifestyle with a stunning courtyard pool and spa, fire pit lounge, outdoor grilling and dining areas, covered bar, state-of-the-art fitness center, and elegant Club Room. Perfectly positioned in the vibrant Naples Design District, this residence is just moments from Gulfshore Playhouse, Baker Park, and the acclaimed restaurants, boutiques, and entertainment of 5th Avenue South, with Naples' pristine Gulf beaches just minutes away. An exceptional opportunity to enjoy the best of downtown Naples living!

1135 3rd AVE S Unit 318, Naples

9115 Strada PL Unit 5205, Naples
$858,000
2 Beds ⋅ 2 Baths ⋅ 226036577 MLS ⋅ The Strada BLDG.
Welcome to coastal sophistication meets effortless living. This Beautifully Furnished 2 Bedrooms and 2 Bathrooms Residence offers a perfect blend of comfort and Style in one of Naples most Vibrant Communities. Designed for Modern Living , the Open Concept Floor Plan features Spacious Living area , Dinning area and an elegant kitchen with granite countertops, stainless steel appliances, an Updated Refrigerator , a gas range stove and tile backsplash deal for entertaining. The primary suite offers a spacious built-in closet and a spa-inspired bathroom with a soaking tub and a separate shower with glass door, while the guest suite provides privacy for visitors with a separate bathroom and a walk-in closet. A Private Patio offers the perfect setting for a morning coffee or a sunset cocktail. Additional highlights include 2 assigned Parking Spaces and a Climate Control Storage Space unit. The separate laundry area is thoughtfully designed with a stackable washer/dryer and built-in cabinetry for storage. The Strada residence enjoy an exceptional amenity package with a 52-foot Rooftop Resort Style Swimming Pool and Spa Hot-Tub, Outdoor/Kitchen Grills, Fitness Center, Fire Pit, Dog park and a Clubhouse with Catering Kitchen, all secured by 24/7 gated and video monitored entry. Just steps away discover the Ritz Carlton Beach Resort , Fine Dining , Boutique Shopping, Whole Foods , Pilates + Cycling studios and a festive Nightlife. All within minutes of downtown Naples and the iconic Naples Pierre. Experience life with Comfort and walkable Convenience at Mercato, your New Beginnings.

9115 Strada PL Unit 5205, Naples

4395 Raffia Palm CIR, Naples
$879,000
4 Beds ⋅ 2.5 Baths ⋅ 226036737 MLS
Tucked between a lush preserve and the sparkle of a resort-style clubhouse, this 4 bedroom, 2.5 bath pool home in Raffia Preserve feels like a well-kept secret. A paver drive, a barrel tile roof, and swaying palms set the tone before you even reach the door. Built in 2015 and meticulously cared for, the home offers 2,233 square feet of light-filled living space finished with crown molding, recessed lighting, and tile throughout. In the kitchen, everyone drifts toward a granite island glowing beneath pendant lights, surrounded by rich wood cabinetry, a tile backsplash, and stainless steel appliances. Sliding glass doors open the evening to a screened lanai with a freeform pool and a south-facing preserve view, along with a covered summer kitchen with a built-in grill, made for lingering dinners under the ceiling fan. The primary suite is a quiet retreat with a recessed ceiling, a dual sink vanity, and a glass-enclosed shower wrapped in tile. Two guest bedrooms share a granite-topped bath, and the fourth bedroom works beautifully as a home office, with a sizable closet that lets it become a guest room, studio, or fitness space. Impact windows throughout and a 2022 generator with a 500 gallon buried propane tank bring calm to every season, and the attached two-car garage offers plenty of room for vehicles and storage. For those with bigger dreams, the laundry room offers potential for a third full bath, and the lanai could be extended toward the backyard for more room to entertain. Beyond your door, gated Raffia Preserve offers a resort pool with water features, a lap pool, a clubhouse, a fitness center, a basketball court, and a playground, with no golf membership required. Set just south of Immokalee Road in North Naples, the community keeps shopping, dining, and the Gulf beaches within easy reach.

4395 Raffia Palm CIR, Naples

36 Las Brisas WAY Unit 37, Naples
$5,250,000
3 Beds ⋅ 3.5 Baths ⋅ 226028455 MLS
Introducing 36 Las Brisas. Extraordinary, effortless living beyond compare. Completely redesigned by Stofft Cooney Architects, Knauf-Koenig Group and Calusa Bay Design, this developer’s personal residence is a singular expression of refined luxury. Every finish and detail has been thoughtfully curated to create a one-of-a-kind home of exceptional beauty, sophistication and ease. Soaring vaulted ceilings, floor-to-ceiling impact glass, exquisite custom millwork and striking architectural detailing define the interiors. Designer wallcoverings, custom window treatments, hand-knotted rugs, wide plank European oak floors, stunning layered furnishings and an exceptional interior and exterior lighting package elevate every space. State-of-the-art control4 technology seamlessly integrates lighting, security, access and sound, with intuitive controls and remote access for effortless management from anywhere. The chef’s kitchen features separate working and seating islands, Wolf and Sub-Zero appliances, a full-size wine refrigerator and extensive custom cabinetry. Three beautifully appointed en-suite bedrooms, 3½ baths and an oversized two-car garage complete this impeccably finished, fully furnished residence. Beyond the walls of glass, a spectacular landscaped and securely gated courtyard creates a private resort-like retreat. Lush tropical gardens, an inviting plunge pool and gracious outdoor living spaces provide an enchanting setting for entertaining or quiet relaxation, seamlessly blending indoor and outdoor living. The villa’s one-of-a-kind design reflects exceptional craftsmanship and thoughtful planning. Natural light illuminates rich textures and finishes, while the open, airy layout balances gracious entertaining with tranquil private retreats. Every space has been designed to be as functional as it is beautiful. In the heart of Pelican Bay, residents enjoy three miles of deeded beachfront, oceanfront dining, extensive tennis and pickleball programs, and exceptional recreational amenities. Located within walking distance to Waterside Shoppes offering world class shopping and dining, Artis Naples, the beach, and minutes from Mercato and Fifth Avenue. With a virtually maintenance-free exterior, this is Naples living at its most refined. A rare opportunity to own a turnkey, designer-furnished residence with the quality and character of a custom estate, paired with the ease of a more intimate footprint. The signature Calusa Bay experience, without compromise. An exceptional Naples address.

36 Las Brisas WAY Unit 37, Naples

5190 Teak Wood DR, Naples
$3,999,000
6 Beds ⋅ 7.5 Baths ⋅ 226036023 MLS
A rare opportunity to own an impressive private estate in sought-after Logan Woods! Situated on over 2.5 acres, this expansive residence, built in 2009, offers 7,639 square feet under air and 11,568 total square feet, providing extraordinary space, privacy, and versatility. An impressive foyer welcomes you into generously proportioned living spaces designed for both grand entertaining and comfortable everyday living. The spacious primary suite features a sitting area, oversized bathroom, and expansive dressing area, creating a private retreat. The well-appointed, catering-size kitchen boasts top-of-the-line appliances, a wine cooler, and ice maker, complemented by a dedicated wine room. A formal living room and dining room provide elegant entertaining spaces, with a see-through fireplace connecting the formal dining room and kitchen. With 6 or more bedrooms and 8 bathrooms, including 6 full baths and 2 half baths, this estate offers exceptional accommodations for family, guests, and multigenerational living. Additional highlights include a huge upstairs balcony overlooking the back yard, a dedicated home office, and a loft above one of the two-car garages, offering flexibility for a variety of lifestyle needs. Step outside to your own private resort-style setting featuring a pool and spa, beautifully landscaped grounds, and gated entry. The expansive property offers a unique combination of space, privacy, and possibilities rarely found so close to Naples' premier shopping, dining, and Gulf beaches. Conveniently located near Waterside Shops, Mercato, Fifth Avenue South, and the Gulf beaches, with easy access to Southwest Florida International Airport, this remarkable Logan Woods estate presents an exceptional opportunity to enjoy spacious estate living in a desirable Naples location.

5190 Teak Wood DR, Naples

7319 Lantana CIR, Naples
$995,000
3 Beds ⋅ 2 Baths ⋅ 226037647 MLS
Discover the art of exceptional living in Olde Cypress! As one of North Naples most-sought after communities, Olde Cypress offers brilliantly remastered Clubhouse with casual and fine dining, championship golf, tennis and pickle ball, bocce courts, pool, fitness center, a vibrant social calendar and a wonderful sense of community, where you instantly belong. Just beyond the community, the very best of Naples living awaits, with world-famous beaches, water sports and boating, nature trails, upscale shopping and dining, art galleries and so much more. Within the community, tucked away amid lush tropical greenery on a peaceful, private lot, this tastefully REFRESHED, move-in ready STOCK Development residence delivers a lifestyle that defines relaxed luxury and offers a perfect balance for indoor/outdoor living. With 3 bedrooms, 2 bathrooms and an oversized 2-car garage, the home also features the following UPGRADES: custom cabinetry, high-end CAFE appliances, exquisite CASHMERE TAJ MAHAL quartzite counter-tops in kitchen and bathrooms, soft color palette, DESIGNER lighting and mirrors, elegant tile flooring and crown molding in living areas, accent wall, hardwood floors in all bedrooms, vaulted ceilings, plantation shutters, hurricane IMPACT glass sliders, windows and doors, and a KOHLER GENERATOR for your peace of mind. As you step outside, a recently REFRESHED, screened-in patio with sparkling HEATED POOL and SPA is a natural extension of the home and an invitation to slow down. A peaceful Naples retreat to call your own. An exceptional lifestyle just outside your door. Welcome home.

7319 Lantana CIR, Naples

1925 Metropolitan BLVD Unit 1204, Naples
$5,100,000
4 Beds ⋅ 4.5 Baths ⋅ 226036189 MLS ⋅ Avra BLDG.
One or more photo(s) has been virtually staged, AI generated or rendered. MOVE-IN READY Q4 2026. A rare opportunity to experience AVRA at Metropolitan Naples beyond the renderings. Residence 04 is nearing completion and has been professionally photographed, offering an authentic first look at the finished interiors, sweeping views, and exceptional scale of this private residence. Set within an exclusive collection of only 56 residences, this four-bedroom, four-and-one-half-bath home encompasses 3,351 square feet of air-conditioned living space and a 549-square-foot terrace, totaling 3,900 square feet of refined indoor and outdoor living. Panoramic views spanning Naples Bay, downtown Naples, and the Gulf provide an extraordinary backdrop, culminating in spectacular western sunsets from the expansive wraparound terrace. The thoughtfully composed split floor plan balances gracious entertaining with privacy, featuring a generous Great Room, private VIP guest suite, and a separate terrace adjoining the owner’s suite. Floor-to-ceiling impact glass frames the surrounding landscape and creates a seamless connection between the interiors and outdoor living spaces. Sophisticated finishes include elegant tile flooring, premium Italian cabinetry, and a chef-inspired kitchen appointed with Wolf and Sub-Zero appliances. Outdoors, a private BBQ grill and integrated wet bar transform the terrace into an extension of the residence, equally suited for intimate evenings or entertaining against the Naples skyline. AVRA presents an elevated collection of private amenities, anchored by a 15th-floor infinity-edge pool, outdoor bar, and social deck overlooking Naples Bay, downtown, and the Gulf. Residents also enjoy a state-of-the-art fitness and yoga center, 24/7 on site concierge, private shuttle service to downtown and the beach, resident lounge with bar and catering kitchen, luxury guest suite, business and conference center, owner’s lounge, putting green, outdoor spa, fire-table seating, BBQ stations, and lush subtropical landscaping. Positioned within Metropolitan Naples, AVRA places 5th Avenue South, Bayfront, Naples Bay, acclaimed dining and shopping, and Naples’ renowned white-sand beaches within minutes. With only 56 residences, AVRA offers a level of privacy and exclusivity rarely found this close to downtown, pairing the intimacy of boutique condominium living with one of Naples’ most desirable locations. Residence 04 is scheduled for completion in Q4 2026. Current photography showcases the actual residence and its progress rather than developer renderings.

1925 Metropolitan BLVD Unit 1204, 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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