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

18630 Royal Hammock BLVD, Naples
$949,000
5 Beds ⋅ 3.5 Baths ⋅ 226039775 MLS
Spectacular sunset views, extensive updates, and exceptional value in Royal Palm Golf Estates! This customized Gulfstream home offers 5 bedrooms, 3½ baths, a 3-car garage, and 3,406 square feet of thoughtfully designed living space. Built in 2007 and meticulously maintained, this spacious Naples home combines comfortable everyday living with an ideal setting for entertaining family and friends. The heart of the home is a generously sized kitchen featuring a large center island and walk-in pantry, providing abundant workspace and storage while creating a natural gathering place for family and guests. The home's spacious layout and inviting indoor-outdoor living spaces make entertaining effortless. One of the home's most captivating features is the spectacular water view, framed by swaying palms and providing a beautiful backdrop for breathtaking SW Florida sunsets throughout the year. Enjoy the scenery from virtually anywhere in the main living areas or step outside to the spacious covered lanai, where you can relax by the pool or unwind in the spa. The extensive list of improvements adds tremendous value and confidence for the next owner. Major updates include a new roof, impact-resistant windows, and electric roll-down shutters across the lanai and front door, all completed in 2018. A central vacuum system was added in 2019, various appliance replacements in 2020 and 2026 and new panoramic screen cage in 2020. In 2025, the entire interior and exterior were freshly painted, a new front door was installed, and all garage door openers were replaced. A detailed list of improvements is available, and to provide even greater peace of mind, the seller is offering a full 1-year HOME WARRANTY to the new owners at closing. Royal Palm Golf Estates offers some of the lowest HOA fees in the area. The golf course is open to the public, with no mandatory membership required, making it easy to enjoy a round of golf without the expense or commitment of a private club. Residents and guests can also enjoy food and refreshments at the clubhouse. If you are searching for a spacious, well-maintained Naples home with beautiful water and sunset views, a large island kitchen, walk-in pantry, private pool and spa, extensive updates, and the benefits of a golf community without mandatory membership fees, this exceptional home deserves your attention. An outstanding combination of location, lifestyle, condition, and value!

18630 Royal Hammock BLVD, Naples

6047 Shallows WAY, Naples
$1,425,000
4 Beds ⋅ 3 Baths ⋅ 226041056 MLS
Renovated in 2025, this fully furnished 4-bedroom plus den, 3-bath pool home in Wilshire Lakes makes an impression from the moment you walk in. Soaring vaulted ceilings and a striking chandelier greet you at the entry, with a clear view through the completely rebuilt kitchen, dining and living areas to the pool and its waterfall. An oversized island anchors the thoughtfully redesigned kitchen, with generous space between the island and surrounding counters so multiple cooks can prep and move comfortably. New flooring and under-cabinet lighting complement the kitchen’s clean, modern design. A Bosch induction cooktop offers fast heating and responsive temperature control, and a Whirlpool double wall oven completes the chef's setup. The den at the front of the home was completely reimagined from the original floor plan. It works beautifully as a home office, an extra space for hosting guests, or a flex room. Before-and-after renovation photos are available upon request or can be viewed during a showing in the home magazine. The expansive, north-facing pool area offers plenty of space to lounge in the sun, dine outdoors, and entertain. A wooded preserve behind the home creates a quiet backdrop. Upstairs, the loft provides a second living area with its own balcony overlooking the outdoors. The balcony could be screened in or enclosed to create additional conditioned space, subject to applicable approvals. The first-floor primary suite features two walk-in closets and a spacious bath with dual vanities, a separate tub and shower, and a private water closet. The primary bathroom offers a clean slate for your own design. A front guest suite can be closed off with a pocket door for added privacy when hosting. The home is offered fully furnished, including an El Dorado dining set with high-back chairs, a newly delivered modern marble coffee table, a brand-new sofa & other furnishings pictured. Both the coffee table and sofa were imported from China. See remarks for select items excluded from the sale. Enjoy Wilshire Lakes amenities with many fun community social events each month without leaving your neighborhood, the community clubhouse, exercise room, pool, tennis and pickle ball courts! Come see how the resort style community, blended with a redesigned layout, flexible living spaces, and preserve-backed pool setting come together at 6047 Shallows Way.

6047 Shallows WAY, Naples

659 98th AVE N, Naples
$995,000
2 Beds ⋅ 2 Baths ⋅ 226041028 MLS
Experience the ultimate Naples coastal lifestyle in this fabulously updated Naples Park residence, where stunning interiors, exceptional outdoor living, and an unbeatable location come together! The showpiece is the BRAND NEW PRIVATE POOL AND SPA, thoughtfully and strategically positioned by the owner to capture sunshine throughout the year, despite the home's northern rear exposure! This spectacular outdoor retreat invites endless days of poolside relaxation, entertaining, and enjoying the Florida sunshine. Step inside to discover beautiful updates throughout, highlighted by a FABULOUS, EXPANSIVE KITCHEN featuring an oversized island, gorgeous quartz countertops, abundant cabinetry, and generous space for gathering and entertaining. The open, flowing floor plan creates an inviting atmosphere, complemented by attractive flooring, plantation shutters, impact-resistant windows and sliding doors, and a stylish dry bar. Currently offering two bedrooms and two bathrooms, the spacious layout provides the easy opportunity to add a third bedroom or den, creating additional flexibility for guests, a home office, or expanded accommodations. LOCATION, LOCATION, LOCATION! Situated in the highly desirable 600 block of Naples Park, this home places you just minutes from the pristine white sands and breathtaking sunsets of Vanderbilt Beach, the Ritz Carlton, LaPlaya Beach Resort, and the fabulous shopping, restaurants, and nightlife of Mercato. Bike to the beach, enjoy sunset cocktails, or explore everything that makes this vibrant coastal neighborhood one of Naples' most sought-after destinations! With NO HOA FEES, PROVEN RENTAL HISTORY, and the flexibility to enjoy as a full-time residence, seasonal retreat, or income-producing investment, this property presents an exceptional opportunity. Beautifully updated interiors, an incredible kitchen, and a spectacular new pool and spa combine to deliver the quintessential Naples lifestyle and located in Flood Zone X!

659 98th AVE N, Naples

506 106th AVE N, Naples
$1,800,000
4 Beds ⋅ 3.5 Baths ⋅ 226036826 MLS
Move in ready and meticulously maintained in highly desirable Naples Park! Location, space and the Southwest Florida lifestyle come together! Situated on an oversized corner lot in the heart of Naples Park, this beautiful single-family home offers the perfect combination of comfort, convenience, and coastal living, ust minutes from the white sandy beaches of Vanderbilt Beach, Wiggins Pass and the upscale shopping, dining, and entertainment at Mercato! Pride of ownership shines throughout which has benefited from thoughtful updates and improvements over the years. This home provides an inviting setting for full-time living, seasonal enjoyment, or as an investment property. Featuring 4 bedrooms, 3.5 bathrooms, den, and an additional flex room currently used as an in-home gym. A unique bonus to this home is an additional walk-in shower in the laundry room, perfect for extra guests, rinsing off after the beach, or even bathing your furry friends! Step outside and embrace the Florida lifestyle with your own private salt water pool. Perfect for relaxing in the sunshine, entertaining guests, or enjoying warm Naples evenings and gorgeous sunsets! Additional highlights include impact resistant windows and doors, a roof less than 10 years ofd, and 2 newer A/C units. And let's talk about location! Naples Park is one of North Naples' most sought-after neighborhoods, offering convenient access to Vanderbilt Beach, Delnor-Wiggins Pass State Park, Mercato, and an abundance of shopping, dining, and recreation. With NO HOA FEES, you'll enjoy the flexibility and freedom of owning a single-family home in this fantastic coastal community. Your Piece of Paradise awaits!

506 106th AVE N, Naples

8158 Lucello TER S, Naples
$1,199,000
4 Beds ⋅ 3 Baths ⋅ 226040993 MLS
Luxury Living – Beautifully Furnished, Turnkey & Ready to Enjoy! Experience the best of luxury living in this stunning, custom-built 4-bedroom plus den residence, completed in 2022 and beautifully maintained to show like new. Used only part-time as a holiday home, this exceptional property offers the feel of a brand-new home with every detail thoughtfully designed for comfort, style, and effortless Florida living. Step outside to your own private backyard retreat, featuring a custom swimming pool within a screened enclosure, with desirable southern rear exposure to enjoy the Florida sunshine. Entertain family and friends in style with a covered outdoor dining area, comfortable outdoor seating space, and a fully equipped outdoor kitchen – the perfect setting for relaxing or hosting year-round gatherings. Inside, you'll discover a beautifully appointed kitchen featuring an oversized island, natural gas stove, and pantry, ideal for both everyday living and entertaining. Additional highlights include impact-resistant doors and windows, a spacious two-car garage, and an abundance of luxurious finishes throughout. Even better, this home is being offered fully furnished and completely turnkey. Simply bring your suitcase and start enjoying the Florida lifestyle from day one! Enjoy the added security of a gated community entrance, along with an impressive array of resort-style amenities, including two community swimming pools, clubhouse, tennis and pickleball courts, fitness room, aerobic studio, social room, kitchen, and inviting fire pit gathering area. Perfectly situated in an excellent location, you'll be just a short ride from the charm and excitement of downtown Naples and the renowned 5th Avenue South, with its upscale shopping, fabulous restaurants, theatre, parks, marinas, and so much more. Whether you're searching for a luxurious seasonal retreat, a full-time residence, or the perfect Florida getaway, this exceptional home delivers the lifestyle you've been dreaming of. Luxury, location, privacy, and convenience – all beautifully wrapped into one extraordinary opportunity!

8158 Lucello TER S, Naples

6677 Hunters RD, Naples
$9,550,000
6 Beds ⋅ 6.5 Baths ⋅ 226041087 MLS
Set behind a gated entrance on 2.5 private acres in Livingston Woods, this exceptional Naples estate brings together two beautifully finished residences, expansive outdoor living, and climate-controlled garages accommodating 10-plus cars. Fully fenced and thoughtfully arranged for privacy, the property offers space for multigenerational living, extended guests, entertaining, and a prized automotive collection. The main residence offers 5,500 square feet of light-filled living with dramatic 16-foot ceilings accented by wood beams, wide-plank oak flooring, and a home office framed by floor-to-ceiling windows. The chef’s kitchen includes Wolf appliances and gas cooking, while a glass-enclosed, climate-controlled wine room creates a striking focal point. The primary suite offers a soaking tub, oversized shower, designer walk-in closet, and private access to the pool and gardens. Additional guest accommodations provide comfort and privacy throughout. A poolside cabana suite features its own lounge area, morning bar, and spa-like shower. The separate guest house, just under 2,000 square feet, lives like a private home with two bedrooms, two bathrooms, a full kitchen, eat-in dining area, spacious living room, laundry, lofted flex room, and private balcony. Separate electric service adds flexibility for independent use. At the center of the estate, a 50-foot gas-heated saltwater pool with a sun shelf is surrounded by approximately 8,500 square feet of sandblasted marble decking. A new outdoor kitchen is currently under construction, complementing the tiki hut, multiple lounging areas, and lush tropical landscaping for outdoor entertaining. For car collectors, the air-conditioned garages feature soaring ceilings, polished floors, and a dedicated lounge overlooking the vehicles. The estate also includes a dedicated home gym with a sauna. The grounds offer room for horses, with an equestrian center just one block away. Designed with efficiency and self-sufficiency in mind, the estate features a private well with whole-house water treatment, foam attic insulation, irrigation throughout the property, and underground propane tanks supplying the gas cooking, pool heating, and whole-house generator. This private estate is conveniently located near Naples’ beaches, dining, and shopping, with access to Southwest Florida International Airport.

6677 Hunters RD, Naples

8977 Crooked Stick CT, Naples
$2,249,000
4 Beds ⋅ 3.5 Baths ⋅ 226040726 MLS
Welcome to this exceptionally remodeled and beautifully furnished 4-bedroom plus den lakefront residence, ideally positioned on a quiet cul-de-sac in the prestigious, double-gated community of The Majors at Lely Resort. Set on one of the premier lots in Majors, this remarkable home offers an exceptional combination of privacy, custom design, and breathtaking lake views, complemented by a deeded Players Club & Spa membership with NO waitlist. From the moment you enter through the elegant double glass front doors, your eyes are drawn to the expansive lake views and the beautifully redesigned interior. This popular Muirfield Great Room floor plan has been transformed into a truly distinctive residence, featuring extensive updates, custom finishes, designer accent walls, and thoughtfully integrated built-ins throughout. Designed for effortless indoor-outdoor living, the spacious great room features expansive pocketing glass sliders that open completely to an oversized covered lanai, creating a seamless extension of the living space. The outdoor setting is equally impressive, featuring a heated swimming pool and spa, outdoor fireplace, fully equipped outdoor kitchen, and multiple covered seating and dining areas. Whether entertaining guests or enjoying a quiet evening overlooking the lake, this private outdoor retreat delivers the best of the Southwest Florida lifestyle. The beautifully updated kitchen features crisp white cabinetry, quartzite countertops, stainless steel appliances, and an inviting open layout that connects naturally with the great room and dining area. Crown molding, recessed lighting, and carefully selected finishes add elegance throughout the main living spaces. The owner’s suite offers a private sanctuary, complete with custom his-and-hers built-in closets, a convenient coffee bar, and a spa-inspired bathroom featuring a spacious walk-in shower and freestanding soaking tub. A thoughtfully designed guest bedroom doubles as an ideal home office or flex space, featuring a custom built-in workspace and a concealed queen-size Murphy bed. Additional highlights include plantation shutters throughout, a private laundry room with utility sink and abundant cabinetry, a 2021 flat tile roof, a climate controlled garage, and storm screens across the rear lanai. Beyond the home, residents enjoy the exceptional amenities of the Players Club & Spa, featuring resort-style swimming pools, a state-of-the-art fitness center, indoor/outdoor dining, a lively Tiki Bar with weekend entertainment, 12 lighted tennis courts, dedicated pickle-ball courts, bocce facilities, and a full calendar of social activities for all ages.

8977 Crooked Stick CT, Naples

1875 Les Chateaux BLVD Unit 302, Naples
$1,375,000
3 Beds ⋅ 2.5 Baths ⋅ 226033185 MLS ⋅ Les Chateaux BLDG.
Beautifully refreshed and move-in ready, this top-floor residence in Les Châteaux at Pelican Marsh has just undergone an extensive update, bringing a fresh, sophisticated look to an already spacious and desirable floor plan. Offering 3 bedrooms plus a den, 2.5 baths, a family room and great room, this residence combines generous living spaces with gorgeous views and an exceptional Pelican Marsh lifestyle. The recent transformation includes new luxury wood-look vinyl flooring throughout the main living areas, new wall-to-wall carpeting in all bedrooms, fresh interior paint including walls and baseboards, and new white Maverick LED ceiling fans throughout the bedrooms, family room, great room and lanai. New satin brass lighting in the entry, dining room and office adds a warm, updated finish. The refreshed kitchen features new quartz countertops, a 33-inch Kohler cast-iron white sink, satin brass faucet and coordinating hardware. With abundant cabinetry and an open connection to the living spaces, the kitchen is designed for both everyday living and entertaining. The primary bath has been beautifully updated with new shower tile and enclosure, quartz countertops, Kohler sinks and polished chrome faucets, freshly painted cabinetry, new polished chrome hardware and accessories, and two Robern 30-by-40-inch lighted mirrors with dimming, cool-light and defogging features. The guest bath received its own refresh with a new shower door, quartz countertops, Kohler sinks and polished chrome faucets, updated accessories and two additional Robern lighted mirrors. One of the home's most appealing features is the enclosed lanai, which provides additional air-conditioned living space and works beautifully as an office, den or quiet retreat while taking advantage of the expansive views. The top-floor location, volume and tray ceilings, plantation shutters and multiple living areas create a bright, open feel that lives more like a single-family home than a condominium. Additional improvements include a newer water heater and an approximately five-year-old air-conditioning system. Les Châteaux is a beautifully landscaped enclave within Pelican Marsh, one of North Naples' most established gated communities. Residents enjoy an impressive array of amenities, including Courtside restaurant with al fresco dining, eight Har-Tru tennis courts, six lighted pickleball courts, three lighted bocce courts, a fitness and wellness center, spa services, organized social activities, and extensive recreational programming. Pelican Marsh Golf Club offers a private 18-hole championship golf course designed by Robert von Hagge, along with practice facilities, a Learning Center and PGA professionals. Golf membership is separate and private. Ideally located near Mercato, Waterside Shops, dining, entertainment and Naples' beautiful Gulf beaches, this newly refreshed top-floor residence offers exceptional space, views and access to one of Naples' most complete country club lifestyles.

1875 Les Chateaux BLVD Unit 302, Naples

50 Seagate DR Unit 904B, Naples
$1,795,000
3 Beds ⋅ 2 Baths ⋅ 226038872 MLS ⋅ Westshore At Naples Cay BLDG.
Gulf views, spectacular sunsets, and sweeping views up Clam Pass. This ninth-floor, end-unit residence at Westshore at Naples Cay captures some of the most beautiful coastal scenery in Naples, with the Gulf of Mexico stretching to the horizon and the beauty of Clam Pass to the north. With three bedrooms, this is the beach retreat you've been looking for, offering plenty of room for guests to visit and the flexibility of weekly rentals when you're not in residence. Naples Cay feels like a private beachfront resort, tucked away behind a staffed, gated entrance and surrounded by lush tropical landscaping, flowering gardens, and winding paths leading to the beach. Spend your mornings walking along the shoreline, afternoons relaxing by the pool or playing tennis, and evenings watching the sun set over the Gulf. With no major public beach access points immediately nearby, this stretch of sand feels wonderfully peaceful, even during Naples' busiest season. The location is another reason Naples Cay is so special. Ride your bike to the waterfront restaurants and boutiques at Venetian Village or to Waterside Shops for shopping and dining. Walk down the beach to the beachfront restaurant at Naples Grande, or simply stay home and enjoy the views. Everything that makes Naples such an appealing winter destination is close at hand, yet once you pass through the gates, the pace feels entirely different. For those seeking an easy-to-enjoy Naples beach home, this residence offers an appealing combination of location, coastal views, resort amenities, and rental flexibility. Arrive, unpack, and settle into the rhythm of life on the Gulf, with the option to generate rental income during the weeks you're away.

50 Seagate DR Unit 904B, 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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