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

2614 L ERMITAGE LN, Naples
$5,450,000
3 Beds ⋅ 3.5 Baths ⋅ 226038774 MLS
A rare opportunity to experience the artistry of a celebrated interior designer awaits in Grey Oaks Country Club. Featured in the recent issue of Florida Design magazine this extraordinary residence is the personal home of interior designer Valerie Grant, who has masterfully transformed its original Tuscan architecture into a sophisticated yet inviting contemporary retreat. Drawing upon her early career in fashion, Grant approached the redesign through textiles, allowing their colors, textures, and interplay to establish the home's distinctive character. Thoughtfully layered contemporary furnishings, collected antiques, original art, and bespoke architectural details, create interiors that feel warm, comfortable, and timeless. Completely reimagined in 2024, this exquisitely furnished, move-in-ready residence offers curated living spaces, including three bedrooms, three-and-a-half baths, a spacious office, and a versatile den thoughtfully designed to serve as both an intimate lounge and an additional guest bedroom when needed. Every room reflects exceptional craftsmanship, with wide-plank white oak flooring, custom millwork, elevated ceilings, designer lighting, and expansive windows framing captivating lake and golf course views. The beautifully redesigned chef's kitchen combines bespoke cabinetry, exquisite quartzite counters, professional-grade appliances, and an antique wood island, while an elegant wet bar welcomes gracious entertaining. Just off the kitchen, a beautifully appointed laundry room doubles as a service kitchen, providing additional preparation space and convenience when entertaining. The serene primary suite offers tranquil water views, beautifully appointed closets, and a spa-inspired bath with exquisite marble tile Upstairs, two guest suites and a private family lounge with coffee bar offer wonderful accommodations for family and friends. Beyond the interiors, an extraordinary outdoor sanctuary invites leisurely afternoons and memorable evenings overlooking the shimmering lake and Pine Course's 18th fairway. A renovated pool and spa, elegant marble decking, a custom motorized pergola with fire table, and a spectacular summer kitchen create a seamless extension of the home's gracious living spaces. Additional enhancements include a new 2024 roof, impact windows/doors, and professionally designed exterior lighting. Situated in a quiet interior location, this exceptional residence offers privacy, sophistication, and effortless Florida living. Grey Oaks Country Club offers an unparalleled lifestyle with three golf courses, two clubhouses, several dining venues, resort-style pool, 30,000 sq.ft. Wellness Center & Spa, tennis, pickleball, bocce, and a vibrant social calendar. Centrally located just minutes from world-class shopping, dining, and beaches, this remarkable residence welcomes you to enjoy the very best of Naples living.

2614 L ERMITAGE LN, Naples

1651 Vinland WAY, Naples
$4,795,000
3 Beds ⋅ 3.5 Baths ⋅ 226038632 MLS
The Landings at Bear’s Paw Luxury Golf Course Living with Private Boat Slip & Immediate Golf Membership Discover an exceptional blend of architectural elegance, refined luxury, and the quintessential Naples lifestyle in this custom ranch-style residence at The Landings at Bear’s Paw. Expertly designed by MHK Architecture and Planning, this beautifully appointed three-bedroom plus den, three-and-a-half-bath home showcases sophisticated craftsmanship and thoughtfully curated details throughout. Step inside to an inviting living space highlighted by soaring cathedral ceilings with beautiful shiplap detailing, creating an atmosphere of warmth and understated elegance. The gourmet kitchen seamlessly combines style and functionality, featuring premium Thermador appliances, exquisite quartz countertops, and custom lighting—an ideal setting for intimate gatherings and effortless entertaining. Beyond the interiors, the scenic backyard offers a private outdoor sanctuary with a sparkling pool and spa, complemented by a spacious lanai. Whether enjoying a quiet morning or entertaining family and friends, this inviting retreat captures the essence of relaxed Florida living. Sweeping views of the third and seventh holes of Bear’s Paw’s prestigious Jack Nicklaus Signature Golf Course provide a stunning backdrop. A private boat slip with Gulf access via the Gordon River adds another dimension to this exceptional lifestyle, offering the freedom to explore Southwest Florida’s waterways. Golf enthusiasts will appreciate the opportunity for immediate golf membership, bringing the pleasures of championship golf right to their doorstep. Just steps away, the Gordon River Greenway Park features scenic nature trails and a boardwalk, perfect for walking, jogging, and biking. Experience the best of Naples living, where luxury, championship golf, private boating, and natural beauty converge. With a private boat slip and immediate golf membership, this exceptional residence presents a rare opportunity to embrace the lifestyle you’ve been waiting for. Schedule your private showing today.

1651 Vinland WAY, Naples

425 Cove Tower DR Unit 403, Naples
$875,000
3 Beds ⋅ 2 Baths ⋅ 226038846 MLS ⋅ Caribe At Cove Towers BLDG.
One or more photo(s) has been virtually staged, AI generated or rendered. Experience the best of luxury coastal living at Caribe at Cove Towers, where breathtaking surroundings, resort-style amenities, and an exceptional North Naples location come together to create the ultimate Southwest Florida lifestyle. Nestled along the tranquil waters of Wiggins Bay, this beautifully renovated 3-bedroom, 2-bath residence offers a sophisticated yet relaxed retreat, perfect for enjoying everything paradise has to offer. Imagine starting your mornings with coffee in your peaceful coastal sanctuary, spending afternoons lounging by the pool or enjoying a day at the beach, and ending your evenings dining at nearby waterfront restaurants or entertaining friends in your beautifully appointed home. Inside, a bright, open-concept floor plan showcases wood-look tile flooring, elegant tray ceilings, contemporary lighting, and a stunning renovated kitchen featuring quartz countertops, stainless steel appliances, and a sleek induction cooktop with hood. The spacious primary suite offers a private escape with custom Closets by Design and a spa-inspired bathroom featuring a modern soaking tub. Thoughtful conveniences include a new elevated LG ThinQ washer and dryer, laundry sink, impact-resistant windows, electric storm shutters, garage parking, and a private, air-conditioned storage room on the lobby level. Beyond your front door, Cove Towers offers a true resort-style experience with a sparkling community pool, fitness center, tennis courts, marina access, EV charging, and the peace of mind of a 24-hour guarded gate. For those seeking an even more elevated lifestyle, optional membership at Tarpon Cove Club provides access to dining, an active social calendar, and a convenient beach shuttle to Delnor-Wiggins Pass State Park. Just minutes from Mercato, Waterside Shops, pristine Gulf beaches, and some of Naples' finest dining and entertainment, this exceptional residence places the very best of coastal living within easy reach. Offered below its recently assessed value, this is an outstanding opportunity to embrace the luxury, convenience, and relaxed elegance of life at Cove Towers.

425 Cove Tower DR Unit 403, Naples

7493 Lantana CIR, Naples
$1,850,000
4 Beds ⋅ 3.5 Baths ⋅ 226038052 MLS
One or more photo(s) has been virtually staged, AI generated or rendered. Experience refined luxury living in the prestigious Olde Cypress community. This beautifully appointed Jasmine II residence offers four bedrooms, three-and-a-half baths, and an elegant floor plan designed for effortless entertaining and indoor-outdoor living spread over 2,867 square feet. The gourmet kitchen features quartz countertops, Carrara marble backsplash, premium Monogram appliances, a five-burner gas cooktop, and rich espresso cabinetry. The sophisticated primary suite boasts hardwood flooring, dual walk-in closets, private lanai access, and a spa-inspired bath with soaking tub and walk-in shower. Two additional guest bedrooms feature hardwood flooring and a connecting bath. Outdoors, a private resort-style retreat awaits with a gas-heated saltwater pool, raised spa, and fully equipped summer kitchen with Alfresco grill. Additional highlights include impact-resistant glass, plantation shutters, Sonos sound system, whole-house Kinetico water filtration, underground propane tank, and a three-car garage. Enjoy the newly renovated & exceptional lifestyle of The Club at Olde Cypress, featuring a P.B. Dye-designed championship golf course, dining, fitness center, resort-style pool, tennis, and pickleball. A remarkable opportunity to embrace luxury Naples living. One or more photo(s) has been virtually staged, AI generated or rendered.

7493 Lantana CIR, Naples

269 Colonade CIR Unit 2802, Naples
$1,250,000
3 Beds ⋅ 2 Baths ⋅ 226038267 MLS ⋅ Colonade BLDG.
Once-in-a-lifetime opportunity to own a piece of paradise in one of the most sought-after coastal communities in the world. Ideally just moments from the world-renowned boutiques, restaurants, and coastal energy of downtown Fifth Avenue, and equally as close to the sugar-white sand and beaches of the Gulf, this first floor residence offers incredible living space within highly coveted Park Shore. From the moment you arrive through the private gated entry of Colonade, a sense of quiet sophistication unfolds. Inside, nearly 2,200 square feet of impeccably curated living space is defined by large volume ceilings, exceptional craftsmanship, and an effortless connection between indoor elegance and the breathtaking natural beauty beyond. Walls of windows and glass throughout, create an uncanny environment of fresh, natural light accompanied by custom white plantation shutters that frame the peaceful and private preserve view, transforming every room into a living portrait of serenity. Designed for intimate moments and unforgettable gatherings, this fully remodeled and immaculately kept home also boasts; three oversized bedrooms, two beautifully appointed full baths, a private 2 car garage with brick paver entry, an inviting Floorplan and the ability to purchase fully furnished/turnkey, if desired. Life here extends far beyond your front door. Feel like shopping, gourmet meals or private beach access? Walk to Venetian Village boutique shops, take a short stroll to nearby fine dining, or enjoy Park Shores private beach club. Steps from the freshly updated Colonade amenity hub, residents also can enjoy an oversized clubhouse area with private kitchenette, wet bar, state of the art fitness center, and heated pool and spa. Boat slips are also available to Park Shore residents at nearby Venetian Bay Yacht Club. In immaculate condition and ready for immediate enjoyment, this is more than a spacious luxury residence, it is an invitation to embrace one of Naples most desired lifestyles.

269 Colonade CIR Unit 2802, Naples

2120 Curtis ST, Naples
$1,750,000
3 Beds ⋅ 3 Baths ⋅ 226038862 MLS
Stunning, contemporary, open concept home with three full en-suite bedrooms. As well as being completely furnished, the owner is willing to convey title to the 2023 Jeep Wrangler and golf cart stored in the garage. Ready for your immediate occupancy and enjoyment this season. The great room has 15 foot celings, skylights, and a kitchen containing almost any upgrade one could dream of for gourmet dining and entertaining - including a large Subzero wine cooler, and a Fisher Paykel 5 burner cooktop gas range, Kinetico reverse osmosis water system and water softener. Operate your blinds with ease, with the Hunter Douglas motorized blinds througout the home. Use the one touch remote or an app that you simply download to your mobile device. Open a wall of glass sliders to enjoy your outside living room. Equipped with a screened-in lanai, TV, heated pool with auto filler, LED lighting, modern Lynx grill and outside refrigerator. Landscape lighting surrounds the home, enlarged 500 gallon buried propane tank, 22KW backup generator, monitored alarm system with hard-wired outside cameras, ring door bell, and garage camera. Two separate air conditioning units are under semi-annual maintenance contracts. One for the entire home and a mini split for the third, very private bedroom and bath, that is perfect for your out of town guests. Hurricane-proof windows and the highest construction standards were used throughout. Nearly maintenance free living as the HOA handles weekly exterior lawn and pool maintenance. Extremely low HOA fee cannot be matched at any other single family home in the area. The home is just a short walk to the well-known Naples Bay Club The facility is world class with every imaginable amenity such as work-out faciity, elegant locker rooms with steam room, spa services, restaurants, three pools, two hot tubs, tennis, discounts on boat rentals, golf reciprocals, and social events year round for the members should you so desire to join the club. Hop on your included street-legal golf cart, turn up the volume on the high-quality stereo, and be downtown in minutes. This is a must see house that is steps away from the famous 5th Avenue South and Third Street South.

2120 Curtis ST, Naples

997 Spyglass LN, Naples
$18,900,000
6 Beds ⋅ 7.5 Baths ⋅ 226038826 MLS
Perfectly positioned along the tranquil waters of Runaway Bay, this beautifully reimagined Port Royal residence offers an elegant blend of contemporary refinement and timeless sophistication. The interiors were thoughtfully transformed with clean, modern finishes, curated fixtures, and exceptional attention to detail—reflecting a globally inspired design aesthetic. A remarkable entry foyer with a striking stairway sets an impressive tone upon arrival, leading to an array of beautifully proportioned living spaces. The formal living and dining rooms are gorgeous and light-filled, while a cozy den with custom built-in shelving provides a warm, intimate retreat. The renovated kitchen, appointed with Ruffino cabinetry and thoughtful upgrades, flows effortlessly into a functional family room and the expansive covered outdoor living area. A custom glass wine room adds a focal point and a touch of understated luxury. The home’s highly functional configuration includes six spacious bedrooms, each with its own ensuite bathroom. The first-floor primary suite offers convenience and privacy, while five additional guest suites are located upstairs along with a large exercise room and a secondary loft office. Upgraded bathrooms throughout further elevate the home’s contemporary feel. Situated on a unique and well-proportioned Port Royal lot, the property features a spacious three-car garage with a large motor court and enjoys an exceptional position on sought-after Spyglass Lane. Boaters will appreciate the property’s no-bridge access to Naples Bay, the Gulf, and the surrounding estuarine waterways. The home’s elevated living experience is further enhanced by updated lighting and AV controls, security cameras, and motorized window shades. An outstanding opportunity to secure a residence in Port Royal and enjoy the newly completed Port Royal Club beachfront clubhouse, offering an exceptional new chapter in luxury coastal living. This property is eligible for Port Royal Club membership.

997 Spyglass LN, Naples

9074 Limestone LN, Naples
$920,000
2 Beds ⋅ 2 Baths ⋅ 226035553 MLS
This beautifully maintained 2BR+Den,2BA is a blissful sanctuarty! New flooring, sophisticated finishes and move-in ready with furniture and golf cart negotiable. Additionally the third room works as a den, office, or flex space. The open kitchen is made for everyday living and entertaining, with a built-in oven and microwave, electric cooktop, abundant cabinetry, generous prep space, and a walk-in pantry! Natural light fills the home throughout, and the sunsets are soothing! This is an oversized private lot, a front lake view, exclusive backyard and an expansive lanai, there's plenty of room to spread out outdoors! The backyard view is a nature preserve, adding privacy for entertaining or blissful moments. Recent updates include a new air conditioning unit (2022) and a freshly epoxied two car garage and a Storm Smart screen on the lanai. Then there's The Quarry itself: a private, gated, Distinguished Club of America 2024. Discover this hidden gem community on the shores of Stone Lake. Enjoy boating, paddleboarding, wakeboarding, and a resort-style beach, plus tennis, pickleball, bocce, and a lively tiki bar. Dine at the indoor restaurant, the casual patio, or the Q-Bar. Stay active with the fitness center, lap pool, walking trails in the Preserve. The Golf course designed by Dr. Michael Hurzdan and Dana Fry was a championship golf course that wraps around the water with eighteen holes of Floridian landscape. Golf memberships are available at the privately owned 18-hole Quarry Golf Club, with no wait list! Quarry Golf is under going turf changes in 2027: reciprocal playing options are available while undergoing renovations.

9074 Limestone LN, Naples

13242 Wedgefield DR Unit 24-9, Naples
$750,000
3 Beds ⋅ 3 Baths ⋅ 226037975 MLS
One or more photo(s) has been virtually staged, AI generated or rendered. EXTENSIVE UPGRADES, YOUR OWN PRIVATE POOL, AND AN EXCEPTIONAL NORTH NAPLES LOCATION JUST MINUTES FROM VANDERBILT BEACH! Welcome to 13242 Wedgefield Drive #24-9, located within the desirable gated community of Imperial Golf Estates, where comfort, coastal elegance, and the ultimate Southwest Florida lifestyle come together. WITH A NEW ROOF, NEW IMPACT WINDOWS AND DOORS, NEW HVAC, AND AN IMPRESSIVE LIST OF MAJOR IMPROVEMENTS ALREADY COMPLETED, THIS 3-BEDROOM, 3-BATHROOM POOL HOME IS AN OPPORTUNITY YOU DON'T WANT TO MISS! Offering 1,980 square feet of living space, this inviting Naples residence features 3 spacious bedrooms, 3 full bathrooms, and a convenient 2-car garage, providing an ideal combination of comfort, functionality, and Florida living. THE BIG-TICKET UPGRADES HAVE ALREADY BEEN DONE! Enjoy peace of mind with an extensive list of improvements, including a NEW ROOF, NEW PLUMBING/PIPING, NEW IMPACT-RESISTANT WINDOWS, DOORS AND SLIDERS, NEW HVAC SYSTEM, NEW ELECTRICAL PANEL, NEW TANKLESS WATER HEATER, NEW PAVERS, AND UPDATED GARAGE DOOR HARDWARE. These significant improvements add exceptional value and allow you to focus on enjoying your new Naples lifestyle. Step outside into your very own PRIVATE SCREENED-IN LANAI AND POOL RETREAT! Whether you're enjoying your morning coffee, soaking up the Florida sunshine, entertaining family and friends, or unwinding after a day at the beach, this inviting outdoor space is designed for year-round enjoyment. The chlorine pool features a NEW POOL HEATER, making it easy to enjoy your backyard paradise throughout the seasons. AND THE LOCATION? IT DOESN'T GET MUCH BETTER! Situated in the heart of desirable North Naples, you're approximately 4 MILES FROM VANDERBILT BEACH, where breathtaking sunsets and sugar-white sand await. Just 3.7 MILES FROM MERCATO, you'll enjoy easy access to upscale shopping, award-winning dining, nightlife, and entertainment. Bonita Springs is only approximately 7.5 miles away, placing even more of Southwest Florida's beautiful beaches, restaurants, and attractions within easy reach. Nestled behind the gates of Imperial Golf Estates, a highly desirable gated community known for its beautifully maintained surroundings, peaceful atmosphere and exceptional location; this property offers a wonderful opportunity to enjoy the Naples lifestyle in a desirable residential setting while remaining close to everything that makes this area so special. Whether you're looking for a primary residence, a seasonal Florida escape, or a beautiful Naples retreat, this home delivers the perfect combination of LOCATION, MAJOR UPGRADES, PRIVATE POOL LIVING, AND COASTAL CONVENIENCE. THE MAJOR UPGRADES ARE COMPLETE. THE POOL IS READY. THE BEACH IS JUST MINUTES AWAY. ALL THAT'S MISSING IS YOU!

13242 Wedgefield DR Unit 24-9, 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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