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

4021 Gulf Shore BLVD N Unit 14, Naples
$11,995,000
4 Beds ⋅ 4.5 Baths ⋅ 226039064 MLS ⋅ Brittany BLDG.
A commanding perspective on Park Shore living, Penthouse 14 at The Brittany showcases panoramic views of the Gulf, Venetian Bay, and Naples skyline from 6,435 square feet of exquisitely finished interiors and 1,950 square feet of wraparound balcony. Reimagined by UpVail and Architectural Wood Expressions, this four-bedroom-plus-den residence pairs exceptional craftsmanship with a distinctive collection of exotic wood finishes imported from Europe. High-gloss fumed eucalyptus lends depth and warmth to the kitchen and dining room, while high-gloss Macassar ebony defines the powder room and foyer bench. The clubroom features lustrous French walnut, complemented by satin fumed eucalyptus in the foyer and master bedroom and bath. High-gloss olive wood enriches the master closets, and satin gray eucalyptus brings understated elegance to the VIP bath. European white oak flooring, quartzite and marble surfaces, and bespoke cabinetry create a cohesive expression of refined coastal living. A full suite of Miele appliances, invisible speakers, and Control4 technology integrates modern convenience throughout. Offered fully furnished, the residence includes private key-secure elevator entry, three deeded parking spaces, a finished deeded cabana, air-conditioned storage, and exclusive rooftop access. Resort-style beachfront amenities and proximity to the boutiques and waterfront dining of Venetian Village complete this extraordinary Naples offering.

4021 Gulf Shore BLVD N Unit 14, Naples

18699 Ensenada DR, Naples
$849,000
3 Beds ⋅ 3.5 Baths ⋅ 226039900 MLS
**EXCEPTIONAL PRIVACY, SWEEPING GOLF VIEWS AND RESORT-STYLE OUTDOOR LIVING!** Set on an oversized homesite overlooking Eagles Lakes Golf Club, this beautifully upgraded 2022 residence offers the appeal of nearly new construction and an extraordinary sense of space, with neighboring homes more than 40 feet away on either side. The outdoor retreat is a showpiece: an oversized custom saltwater pool and spa by Slusser Pools, accented by elegant fountains, pearly-azure glass tile and a cascading waterfall. A panoramic picture-window screen enclosure frames expansive fairway views, while the reinforced concrete deck offers low-maintenance durability. The spacious covered lanai is designed for entertaining, complete with an outdoor kitchen featuring a Bull grill, convenient pool bath and motorized hurricane shade. Inside are three bedrooms, two full and two half baths, plus a flexible room ideal for an office, den or formal dining room. A screened front entry welcomes fresh breezes; luxury vinyl plank flooring enhances the main living areas, with tile in the primary bath and laundry. The kitchen offers upgraded LED lighting and under-sink water filtration. In the primary suite, you'll find ample space, and a large window with electric shade. **A RARE FIND: the EXTRA-DEEP THREE-CAR GARAGE** provides exceptional room for vehicles, a boat, golf carts, recreational gear and all the toys that make Florida living fun. Additional features include impact-resistant windows and doors, generator transfer switch wiring, an instant water heater in the primary bath and a 2026 Pentair remote pool control system. The home also has an electric storm screen on the patio. A transferable home warranty through March 2027 includes pool equipment coverage. Located in Royal Palm Golf Estates, the home is convenient to downtown Naples, Marco Island, fine dining, shopping, boating and Gulf beaches. Eagles Lakes Golf Club offers optional annual membership and public tee times, along with a clubhouse bar and grill, driving range and pro shop. Enjoy the rare combination of privacy, modern comforts, spectacular outdoor living and tranquil golf course views.

18699 Ensenada DR, Naples

4867 Cerromar DR, Naples
$1,150,000
3 Beds ⋅ 2 Baths ⋅ 226039368 MLS
Rare opportunity to enjoy bundled golf on an Arnold Palmer-designed course in the award-winning Naples Lakes Country Club, a private, gated, member-owned community where full golf membership is included with every home. Offering world-class amenities in a luxurious setting, this exceptional community provides an unparalleled golf and country club lifestyle. Featuring picturesque golf course views, a private heated pool and spa, this inviting residence offers three bedrooms, two full baths and 2,325 square feet of thoughtfully designed living space. A paver driveway creates an attractive first impression, while French entry doors open to a welcoming foyer accented by decorative ceiling soffits and a chandelier. Inside, tile flooring flows throughout the main living areas, complemented by tray ceilings, recessed lighting and elegant architectural details. The spacious living room features a tray ceiling, ceiling fan and expansive sliding glass doors overlooking the pool, creating a seamless connection between indoor gathering spaces and the outdoor setting. The adjoining dining room offers an inviting atmosphere for entertaining, enhanced by a tray ceiling and chandelier. The kitchen features Coriancountertops with a tile backsplash, recessed lighting, a breakfast bar, cooktop, a wall oven, and a microwave. A separate breakfast nook provides a comfortable setting for casual dining. The primary suite offers a peaceful retreat with carpeting, a tray ceiling, textured ceiling detail, window coverings and two walk-in closets. Its spacious en-suite bath features stone countertops, dual sinks, a large vanity mirror, plantation shutters, a separate shower and a soaking tub. Two additional guest bedrooms provide comfortable accommodations with carpeting and window treatments, including plantation shutters. The guest bath features tile flooring, decorative wallpaper and a glass-enclosed bathtub and shower combination. A dedicated laundry room adds everyday functionality with a utility sink, built-in drying rack and storage cabinetry. Residents of Naples Lakes Country Club enjoy an exceptional collection of amenities, including an Arnold Palmer-designed championship golf course, recent pool and recreation area renovation project featuring a brand-new private resort-style pool and the new Cabana Cafe, a recently renovated turf care center, fitness center, pickleball courts, resort-style pool, tennis courts and bocce. The elegant clubhouse showcases beautiful lake and golf course views, with a variety of dining venues ranging from intimate formal dinners to relaxed outdoor gatherings. With full golf membership included, outstanding recreational amenities and a vibrant country club atmosphere, this residence offers an appealing combination of private outdoor living, scenic fairway views and the sought-after Naples golf lifestyle.

4867 Cerromar DR, Naples

13935 Old Coast RD Unit 501, Naples
$4,050,000
3 Beds ⋅ 3.5 Baths ⋅ 226039095 MLS ⋅ Kalea Bay Tower 300 BLDG.
RESORT LIVING ABOVE THE GULF, WITH EVERY DETAIL DESIGNED FOR AN EFFORTLESS NAPLES LIFESTYLE! Set within the extraordinary resort-style setting of Kalea Bay, Residence #501 offers an elegant home base for enjoying the best of Naples - sunset skies, rooftop living, wellness, dining, recreation and the effortless rhythm of coastal life. This 3-bedroom plus den, 4-bath waterfront residence offers approximately 3226 square feet of refined coastal living, with elevated sunset views that stretch across the Southwest Florida horizon. Floor-to-ceiling glass fills the open-concept great room, kitchen, and primary suite with natural light and frames the view from nearly every room. From this height, you’ll enjoy a front-row seat to golden sunsets, passing boats, and dolphins gliding by. The chef-inspired kitchen is made for entertaining, and the versatile den works as a home office, media room, or guest retreat. Each bedroom has its own en suite bath, giving family and guests comfort and privacy. Step onto the expansive terrace, your private outdoor living room, where the coastal breeze does the rest. Beyond your door, Kalea Bay delivers a true private-club experience. Spend your days at the resort-style pool and waterfront cabanas, or unwind at the spa and wellness center. Stay active in the state-of-the-art fitness studio, with yoga and wellness programming to restore body and mind. Gather with friends at the clubhouse, then enjoy casual or elegant dining without leaving the community. A concierge-style team handles the details so you can simply enjoy. Whether it’s your full-time home, seasonal escape, or second residence, Residence 501 is built for a lock-and-leave lifestyle. Travel with confidence knowing your home is secure, maintained, and ready when you return. Simply turn the key and go. Close to Southwest Florida’s best beaches, boating, golf, shopping, and fine dining, this is elevated coastal living at its best. Schedule your private tour of Tower 300, Residence 501 today.

13935 Old Coast RD Unit 501, Naples

945 Chimney Rock RD, Naples
$4,850,000
4 Beds ⋅ 5.5 Baths ⋅ 226039019 MLS
One or more photo(s) has been virtually staged, AI generated or rendered. Seagate Development Group and Theory Design proudly introduce the Furnished Hartford Model at Opus Stone, one of Naples’ newest gated communities. Showcasing a tailored modern classic design, the Hartford blends timeless architecture with contemporary finishes, creating a sophisticated yet inviting residence defined by thoughtful details and exceptional craftsmanship. The Hartford’s interiors combine classic architectural elements with modern design. Elegant paneled accent walls, crown molding, and streamlined millwork establish a timeless foundation, while natural materials, layered textures, and a carefully curated color palette bring warmth and character throughout the home. Wide-plank light white oak flooring complements substantial 10-inch baseboards and refined door and window casings. A distinctive combination of walnut, white oak, and linen-colored cabinetry adds depth and visual interest while maintaining a cohesive aesthetic. Aged brass, matte black, and chrome accents provide contrast, while black-painted three-panel interior doors with chrome hardware offer a striking finishing touch. Each space has been designed to create a seamless connection between architectural detail, functionality, and everyday living. Situated within the intimate gated community of Opus Stone, the Hartford offers an opportunity to enjoy estate-style living in a desirable North Naples location. Residents benefit from convenient access to Gulf beaches, upscale shopping, fine dining, and entertainment. Renowned private golf clubs, including Olde Florida Golf Club and Calusa Pines Golf Club, are also nearby. Opus Stone features a collection of thoughtfully designed estate floor plans, offering buyers the opportunity to personalize a residence to complement their individual lifestyle and preferences. Discover the Hartford Model at Opus Stone and experience the signature craftsmanship, architectural character, and attention to detail that distinguish Seagate Development Group and Theory Design. Home will be completed Fall 2027.

945 Chimney Rock RD, Naples

597 3rd ST N, Naples
$9,450,000
6 Beds ⋅ 6.5 Baths ⋅ 226039858 MLS
A hidden retreat in the heart of Old Naples. Tucked away at the end of a quiet, dead-end street shared by just four properties, this exceptional lakefront residence offers a rare combination of privacy, tranquility, and proximity to Naples' most celebrated destinations. Custom built in 2013 and offered for sale for the very first time, the home is thoughtfully set back from the street, creating a secluded sanctuary just moments from the beach, Four Seasons, and the charm of downtown Naples. Designed for both gracious entertaining and everyday comfort, the residence features four en-suite guest bedrooms, a spacious primary suite, private office, and additional loft area. The outdoor living experience is equally captivating, with a covered lanai, pool and spa overlooking the peaceful lake, a charming koi pond, and private dock. One of the property's most distinctive features is its detached guest suite, complete with a bedroom, full bathroom, and kitchenette. This thoughtfully designed accommodation offers exceptional flexibility for visiting family, extended guests, or live-in staff, providing privacy and independence from the main residence. With only four properties along this secluded stretch of Third Street North, opportunities to own in this intimate lakefront setting are exceptionally limited. A truly unique offering, combining the serenity of a private waterfront retreat with the convenience of Old Naples living.

597 3rd ST N, Naples

564 41St AVE NW, Naples
$960,000
5 Beds ⋅ 4 Baths ⋅ 226038687 MLS
Experience modern living on 2.50 private acres in Golden Gate Estates, with a canal along the rear of the property. This home features 5 bedrooms, including one that can serve as a home Office, and 4 full bathrooms. The spacious entryway and welcoming foyer create an inviting first impression. The attached mother-in-law suite includes its own bedroom, kitchen, full bathroom, private entrance, and independent A/C system, while the main house has its own separate A/C system. The main kitchen showcases custom double cabinetry complemented by LED under-cabinet lighting, quartz countertops, BUILT-IN DOUBLE OVEN, waterfall island and walk-in Pantry. The primary suite includes a bathroom with dual vanities and walk-in shower, along with separate his-and-her walk-in closets. The bedroom is also pre-wired for bedside reading lights on both sides. One of the four bathrooms provides direct access to the covered lanai, enhancing convenience for outdoor living and future pool installation. The outdoor area also features a fully equipped summer kitchen with a grill and an outdoor shower. Pavers throughout front entryway. Additional features include a Metal roof with SPRAY FOAM INSULATION for improved energy efficiency, porcelain tile flooring throughout, high ceilings, ALL IMPACT RESISTANT WINDOWS AND DOORS, Ring doorbell, raised TV connections, floor outlets, contemporary fixtures, soffit and accent lighting, exterior electrical pre-wiring for future security cameras and holiday lighting, a 500-gallon REVERSE OSMOSIS WATER SYSTEM storage tank, and EV charger-ready wiring in the garage. With 2,646.57 sq. ft of air-conditioned living area and 3,602.83 sq ft under roof, this property offers ample indoor and outdoor space for entertaining, versatile living arrangements, relaxing and future additions. No HOA. Don't miss this rare opportunity to own a future-ready, luxury home in Golden Gate Estates.

564 41St AVE NW, Naples

5935 Barclay LN, Naples
$1,699,000
4 Beds ⋅ 4 Baths ⋅ 226039513 MLS
PRIVATE COURTYARD ESTATE — RENOVATED GUEST CASITA — RESORT-STYLE POOL & SPA — NEW ROOF — SOUTHERN EXPOSURE! Experience elegant indoor-outdoor living in The Strand, one of North Naples’ premier gated golf and country club communities. Offering 3,573 square feet, FOUR BEDROOMS PLUS A DEN, FOUR FULL BATHROOMS, and a THREE-CAR GARAGE, this distinctive residence centers around a private 1,500-SQUARE-FOOT SCREENED COURTYARD. A sparkling pool with FOUR WATERFALLS, a spa, and generous outdoor living areas create an inviting retreat for entertaining or quiet relaxation. The RENOVATED GUEST CASITA features a separate entrance, one bedroom, a walk-in closet, a brand-new bathroom, a FULL KITCHEN, and a spacious living area—ideal for extended stays or private guest accommodations. Inside the main residence, soaring ceilings, coffered and tray details, crown molding, graceful archways, and plantation shutters complement the bright, OPEN-CONCEPT living spaces and kitchen. The FIRST-FLOOR PRIMARY SUITE provides everyday convenience, while two upstairs bedrooms include an oversized bedroom/bonus room, complemented by a balcony overlooking the pool. Recent improvements include a NEW ROOF, NEW FRONT DOOR, freshly painted interiors and exterior, added recessed lighting, and a NEW POOL PUMP AND POOL LIGHT. Beyond your courtyard retreat, The Strand’s beautifully landscaped grounds and welcoming country club atmosphere offer an exceptional Florida lifestyle. Residents enjoy a CLUBHOUSE, THE STRAND CLUBHOUSE POOL WITH RESORT-STYLE AMENITIES, TENNIS, PICKLEBALL, BOCCE, FITNESS FACILITIES, dining, and an active social calendar, with OPTIONAL GOLF MEMBERSHIP for those seeking time on the fairways. A beautiful blend of architectural character, flexible living space, and courtyard privacy in a desirable North Naples setting.

5935 Barclay 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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