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

4041 Gulf Shore BLVD N Unit 206, Naples
$1,599,000
3 Beds ⋅ 3 Baths ⋅ 226039082 MLS ⋅ Savoy BLDG.
Experience the beauty of beachfront living at The Savoy in prestigious Park Shore, where Gulf views, expansive outdoor living spaces, and an exceptional Naples lifestyle come together. This light and bright, beautifully updated and spacious residence offers 2,310 square feet of living space, 3 bedrooms, 3 full bathrooms, and captivating Gulf views from nearly every room. One of the home's most distinctive features is its remarkable collection of private balconies, accessible from the main living area, kitchen, primary suite, and both guest bedrooms, creating an effortless connection to the outdoors. Natural light fills the thoughtfully designed interior, where generous living and dining spaces provide an inviting setting for everyday comfort and entertaining. The beautifully appointed kitchen features white cabinetry, granite countertops, new stainless KitchenAid appliances, a breakfast bar, and a charming breakfast area overlooking the tropical surroundings. The spacious primary suite offers a private balcony, generous walk-in closet, and an expansive en-suite bath with dual vanities, a jetted soaking tub, and separate shower. 2 additional guest bedrooms, each featuring private balcony access and its own walk-in closet, provide exceptional comfort and privacy. With abundant storage throughout, this residence offers the space and functionality rarely found in condominium living. Additional highlights include impact-resistant windows and doors, a spacious laundry room in the residence, and an assigned garage parking space. The Savoy offers an exceptional array of resort-style amenities, including direct beach access, a beachfront pool and spa, an expansive BBQ deck located on the same floor as the unit, a fully equipped fitness center overlooking the Gulf, tennis and pickleball courts, concierge services, guest accommodations, a community room available for residents to rent for events, library, bocce courts, beach chair storage area, and beautifully maintained grounds. Ideally situated along the pristine shores of Park Shore, this residence places the best of Naples within easy reach, including the upscale shopping, waterfront dining, and entertainment of Venetian Village just across the street! Discover a rare opportunity to enjoy spacious coastal living, beautiful Gulf views, and the convenience of a premier beachfront address.

4041 Gulf Shore BLVD N Unit 206, Naples

101 8th ST S Unit 302, Naples
$829,000
2 Beds ⋅ 1 Baths ⋅ 226034568 MLS ⋅ Soce Flats BLDG.
MOTIVATED SELLER HAS REDUCED PRICING SIGNIFICANTLY TO SELL!! The ultimate downtown lifestyle awaits at SoCe Flats. Own newer 2021 fresh construction while having quick walkability to 5th Ave. S. dining, the sugar sand beaches and all that charming Olde Naples has to offer! Perched on the top floor of this highly coveted boutique building, this stunning two-bedroom unit features the development’s most spectacular outdoor footprint—an expansive, wrap-around balcony offering front-row seats to brilliant Gulf Coast sunsets. Every room effortlessly transitions to its own balcony space and exudes coastal-contemporary interiors—thoughtfully designed by Clive Daniel Home. This turnkey residence is unique with rare, short-term rental-friendly zoning, offering the ultimate flexibility to generate income or keep it entirely as your private sanctuary. Enjoy peace of mind with added income when you're not staying in your home or don't rent it out at all. Use any rental management company or rent the unit out on your own, the zoning gives you these options. This top floor two bedroom unit is on the same floor as the rooftop outdoor kitchen and TV lounge. Conveniently grill outdoors and close to your unit at the beautiful grilling station. Unit comes with Clive Daniel furnishing package as well as all housewares, artwork, bedding, rugs, linens, beach chairs, beach cart, etc. Extra owner lock closet in unit and building is pet friendly to owners. An additional assigned owner storage locker on same floor and a covered, assigned parking space are included with the property. The chance to own your Olde Naples getaway and income generator is here!

101 8th ST S Unit 302, Naples

7037 Verde WAY, Naples
$4,950,000
4 Beds ⋅ 4.5 Baths ⋅ 226037686 MLS
Nestled among just 38 residences on picturesque, tree-lined Verde Way, this beautifully remodeled and expanded 4-bedroom, 4.5-bath home lies within the guard-gated community of Isle Verde in Pelican Bay. Located on the Pelican Bay golf course, the residence enjoys the added distinction of being located in FEMA Flood Zone X500—outside the designated high-risk flood zone—a particularly desirable feature in a coastal community. Designed for both everyday comfort and effortless entertaining, the home offers generous living spaces that flow naturally to the outdoors. Step outside this courtyard style home to your private swimming pool and embrace the Southwest Florida lifestyle. Guests can have their own space in their private casita featuring a bedroom and bathroom with a separate entrance. Surrounded by mature trees and lush tropical landscaping, the property exudes a peaceful, park-like atmosphere that perfectly complements its exceptional golf course setting. Pelican Bay centers on nearly three miles of private Gulf beaches, accessible by a quick tram ride or a leisurely stroll along boardwalks through preserved mangroves. Beach attendants set up loungers and umbrellas, while two private beachfront restaurants—Marker 36 on the North Beach and the Sandbar on the South Beach—invite you to linger over lunch or sunset dinner. Racquet facilities, community parks, a fitness center, and the Community Center complete the lifestyle in a community long regarded as a model of environmental stewardship. Adding to its exceptional appeal, Pelican Bay is also home to Artis—Naples, a premier cultural destination featuring the Naples Philharmonic and the renowned Baker Museum. Just moments away, Waterside Shops offers an upscale, open-air shopping and dining experience with luxury boutiques and beautiful tropical surroundings. From pristine beaches and outdoor recreation to world-class arts, entertainment, shopping, and dining, Pelican Bay truly embodies the best of the Naples lifestyle.

7037 Verde WAY, Naples

6932 Cocoplum ST, Naples
$1,575,000
3 Beds ⋅ 3 Baths ⋅ 226033394 MLS
Exceptional southern exposure, breathtaking preserve and water views, and one of the most desirable homesites in Winding Cypress set the stage for this highly upgraded Pinnacle residence. Originally selected with a $125,000 lot premium, this exceptional property is tucked away on a quiet cul-de-sac street and offers a rare combination of privacy, natural beauty, and refined Naples living. Far beyond the standard Pinnacle floor plan, the home features soaring ceilings, expansive living spaces, abundant storage, and a sophisticated kitchen designed for entertaining with an oversized island, wine cooler, natural gas cooking, and impressive walk-in pantry. The private owner’s wing offers a spacious retreat with an oversized walk-in closet. A three-car, fully air-conditioned garage provides exceptional versatility, whether used for vehicles, additional storage, a workshop, or climate-controlled space for prized possessions. The outdoor living experience is equally impressive. Coveted southern exposure fills the lanai with beautiful natural light while providing comfortable year-round enjoyment. Relax in the saltwater pool and spa with sun shelf, entertain from the outdoor kitchen, or simply take in the peaceful preserve and water views. Impact-resistant windows and doors and a whole-home generator provide additional peace of mind. Winding Cypress offers more than 800 acres of natural preserves and an outstanding collection of resort-style amenities, including a 17,500-square-foot clubhouse, resort pool and spa, fitness center, Barefoot Bar & Grill, tennis, pickleball, bocce, dog park, community garden, boardwalk and more, all with lawn maintenance included and a staffed gated entrance. Ideally located near US-41 and I-75 with convenient access to Fifth Avenue South, Third Street South, Naples beaches, and Marco Island. This is elevated Winding Cypress living in a truly exceptional setting.

6932 Cocoplum ST, Naples

7048 PELICAN BAY BLVD Unit 104, Naples
$758,000
2 Beds ⋅ 2 Baths ⋅ 226037715 MLS ⋅ Calais BLDG.
Discover the best of Naples, Florida living in this inviting first-floor, low-rise condo in the desirable Calais community of Pelican Bay. This is the best value in this community as well as the lowest price! Offering 2 bedrooms, 2 bathrooms, and 1,676 square feet of living space, this residence combines comfort, convenience, and a beautiful golf course setting with tranquil lake views. This property can also be rented out for 90 days, 3x a year and 1 small pet is also welcome! A thoughtfully designed floor plan offers comfortable spaces for everyday living and entertaining, while the glass-enclosed lanai provides a peaceful retreat to relax and enjoy the surrounding views. The eat-in kitchen features abundant cabinetry for storage, and the bathrooms have been updated adding both style and functionality. This unit lives like a small villa with the attached one-car garage. Calais residents enjoy a wonderful array of community amenities, including a heated swimming pool, spa, fitness room, and clubhouse with social and gathering spaces. The location also offers convenient walking access to the Pelican Bay tram, making trips to the spectacular white-sand beaches effortless. Living in Pelican Bay is about more than owning a home—it's embracing a sought-after coastal lifestyle. Enjoy private beach access, beachfront dining, scenic walking and biking paths, pickleball, tennis, and opportunities to make new friends within a vibrant community. Whether you're searching for a year-round residence, a seasonal Naples retreat, this Calais residence offers an appealing opportunity to make Pelican Bay your own. Some photos are AI Enhanced

7048 PELICAN BAY BLVD Unit 104, Naples

1645 Bonita CT, Naples
$7,995,000
4 Beds ⋅ 5.5 Baths ⋅ 226039653 MLS
**WINNER of the prestigious Sand Dollar Award for BEST Kitchen and BEST Design** Introducing the only opportunity of its kind in Naples: A chance to own a new construction, never-lived-in, exquisitely furnished residence on navigable water in this competitive price range. Unparalleled luxury and design, as envisioned by Broad Avenue Studios, and brought to life by MHK Architecture and C&E Builders, awaits in this 4,470 sq. ft. waterfront haven in Royal Harbor, one of Naples’ most sought-after neighborhoods. Thoughtfully curated down to every detail, the interiors combine 4 ENSUITE bedrooms, plus a den and 6 baths with generous living spaces, a gourmet kitchen with butler's pantry and a striking bar with black metal and glass hanging shelves. Rich wood tones, architecturally-detailed ceilings, reeded cabinetry, bright marble coating on the counters, matte black metal accents, and polished chrome fixtures create an unforgettable backdrop for upscale living and entertaining on the water. A sun-drenched Florida room, summer kitchen, and heated pool/spa surrounded by a wood deck, complete the picture of this chic-yet-tranquil Naples retreat. Set mere minutes from the beach and downtown's vibrant 5th Avenue, this property brings together all of the qualities of a first-class Naples location where you can enjoy shopping, dining and sunsets within minutes of your front door. Park your boat out back and your home becomes your launchpad to the Gulf of Mexico, plus you are just 6 minutes to Naples Executive Airport!! The location and style of this home truly has it all!

1645 Bonita CT, Naples

188 Cheshire WAY, Naples
$2,950,000
3 Beds ⋅ 3.5 Baths ⋅ 226038932 MLS
Beautifully maintained home with spectacular lake and golf course views, ideally situated within North Naples’ coveted Audubon Golf & Country Club. This spacious residence offers 3 bedrooms plus a den, 3.5 baths, a 3-car garage, NEW 2025 ROOF, NEW 2026 GENERAC GENERATOR WITH A 500-GALLON BURIED PROPANE TANK, and fresh exterior paint (2026). Upon entering, you are greeted by soaring ceilings, beautiful marble flooring, and an abundance of natural light streaming through French doors and expansive picture windows throughout the home. Step outside to your private outdoor oasis, featuring a spacious lanai with ample lounging and entertaining space, a pool with a water feature, and a relaxing spa. A newer picture screen enclosure allows for unobstructed views of the tranquil lake and lush golf course. The well-appointed chef’s kitchen features custom wood cabinetry, granite countertops, dual sinks, a built-in desk, breakfast bar, and a separate eat-in dining area. The spacious primary suite offers private access to the lanai, expansive wraparound picture window, room for a sitting area, and an ensuite bath complete with dual vanities, a dedicated makeup vanity, separate soaking tub, and walk-in shower. Ideally located just minutes from Mercato and Naples’ world-class beaches, Audubon offers an exceptional gated and guarded lifestyle with an 18-hole championship golf course, tennis, pickleball, three new regulation-length bocce courts with a spacious seating area, a new croquet court with seating, a scenic bayside boardwalk, and a poolside club and café featuring a beautifully appointed fitness center. The main clubhouse is currently undergoing extensive renovations.

188 Cheshire WAY, Naples

380 Sharwood DR, Naples
$1,959,900
3 Beds ⋅ 2.5 Baths ⋅ 2026045426 MLS
EXCEPTIONAL CANAL WATERFRONT LUXURY IN PRESTIGIOUS PALM RIVER ESTATES! Welcome to this extraordinary, completely reimagined waterfront residence on beautiful Sharwood Drive in Naples, Florida. Surrounded by stunning homes, this desirable neighborhood offers a gated-community feel without the restrictions. NO EXPENSE WAS SPARED in the complete top-to-bottom renovation of this remarkable two-story home, offering 3 bedrooms plus a den, 2.5 bathrooms, and a 2.5-car garage. Step inside to discover sophisticated finishes, elegant design, and exceptional craftsmanship throughout. The elevated first-floor living area offers added protection against potential flooding. The SHOWSTOPPING DESIGNER KITCHEN features European-style cabinetry, exquisite Taj Mahal countertops, premium stainless steel appliances, a wine refrigerator, and a dedicated coffee station. The MAIN-FLOOR PRIMARY SUITE overlooks the sparkling pool and features a luxurious, spa-inspired ensuite bathroom. Upstairs, two spacious bedrooms, a versatile den currently used as an additional sleeping area, and a full bathroom provide comfort and flexibility. Outside, enjoy your PRIVATE ACCESS WATERFRONT OASIS, featuring a beautiful swimming pool and picturesque canal views, perfect for relaxing, entertaining, and enjoying Southwest Florida's boating lifestyle. Additional upgrades include HURRICANE-IMPACT WINDOWS AND SLIDERS, NEW A/C, NEW POOL HEATER, AND NEW WELL The 2.5-car garage features epoxy flooring and access to a rare BASEMENT-STYLE STORAGE AREA, offering exceptional additional storage space. SOLD COMPLETELY FURNISHED AND TURNKEY! Currently operating as a successful vacation rental, this exceptional Gulf-access waterfront property offers an incredible opportunity for buyers seeking a luxurious primary residence, seasonal retreat, or income-producing investment. Move right in or continue operating it as a vacation rental! Ideally located near Naples' beautiful beaches, world-class dining, shopping, and golf. THIS IS NOT YOUR TYPICAL RENOVATION — IT'S A COMPLETE TRANSFORMATION WHERE LUXURY, QUALITY, AND WATERFRONT LIVING COME TOGETHER!

380 Sharwood DR, Naples

11949 Gardenia AVE, Naples
$1,150,000
3 Beds ⋅ 3 Baths ⋅ 226039409 MLS
LOCATION...LOCATION...LOCATION-3-minute walk to all amenities! This stunning Pearl model home with EXTENDED LIVING SPACE offers an unparalleled blend of luxury and comfort in the highly sought-after Valencia Trails, Naples' premier 55+ community. From the moment you step inside, the soaring 14-foot ceilings and shiplap create an immediate sense of sophistication. The open-concept design seamlessly connects the kitchen and living areas, making it ideal for both everyday living and elegant entertaining. The chef's kitchen is a true showpiece, featuring quartz countertops and backsplash, a natural-gas stovetop, premium stainless-steel appliances, and an upgraded pantry. Level 3 wood cabinetry with soft-close functionality and elegant molding adds a touch of refinement, while ample recessed lighting enhances the space. Step outside to your private screened lanai and extended patio and take in the breathtaking lake views that set this home apart. Whether you're enjoying a quiet morning coffee or hosting guests for an evening gathering, this tranquil retreat offers a seamless blend of indoor and outdoor living. With ample yard space to accommodate a custom pool, a lanai pre-plumbed for an outdoor kitchen, this home is designed for relaxation and entertaining at its finest. LARGE FORMAT EUROPEAN PORCELAIN THOUGHOUT THE HOME, not a builder product; throughout, it makes a seamless flow. For peace of mind, hurricane windows/doors and Central Security/Smart home. The home is equipped with E/V and upgraded power panel. Beyond your doorstep, a three-minute walk takes you to all that Valencia Trails offers —world-class amenities that enhance an active, social lifestyle. The impressive 43,000-square-foot clubhouse features a full-service restaurant and bar, a state-of-the-art fitness center, a full-service salon and spa, and multiple recreational spaces, including card rooms, an art studio, and a learning kitchen. For those who love outdoor activities, the community boasts a resort-style pool, a lap pool, a resistance pool, six tennis courts, eight pickleball courts, and scenic walking and biking trails. Even your four-legged companions will feel at home with two dedicated dog parks just a short walk from the home. This is more than just a home—it's an opportunity to embrace a luxurious, resort-style lifestyle in one of Naples' most exclusive communities. Homes like this are rare, and demand for Valencia Trails continues to grow. Don't miss your chance to own a piece of paradise. Call today to schedule your private tour and experience the elegance, comfort, and breathtaking lake views for yourself."

11949 Gardenia AVE, Naples

Start Your Search

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.

How much is your home worth?

Get instant property value now!