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

813 Wildwood LN, Naples
$765,000
2 Beds ⋅ 2 Baths ⋅ 226036263 MLS ⋅ Bears Paw BLDG.
Experience breathtaking lake-to-golf-course views from this beautifully remodeled, first-floor, furnished 2-bedroom, 2-bath condominium at Bears Paw Country Club. An expansive, air-conditioned Florida room provides the perfect setting to relax and enjoy the picturesque surroundings, with a floor-to-ceiling window and sliding glass door that fill the space with natural light. The open-concept kitchen features custom white raised-panel cabinetry, a pantry, stainless steel appliances, granite countertops, and bar seating, ideal for both everyday living and entertaining. Additional highlights include tile flooring throughout and a wet bar with a built-in wine cooler. The primary suite offers a generous walk-in closet and a beautifully appointed bath with a dual-sink vanity and walk-in shower with seamless glass doors. An exceptional opportunity to secure an immediate Bears Paw full golf membership upon closing. Enjoy the outstanding country club lifestyle with access to the new state-of-the-art clubhouse and fitness center, Jack Nicklaus Signature Golf Course, bocce, pickleball, tennis, dog park, driving range, two putting greens, and a private marina with Gulf access. A golf cart is included, along with a dedicated cart garage conveniently located next to your assigned covered parking space. The 24-hour gated and manned community offers a walking and biking path to downtown Naples, is less than three miles from the beach, and is located within the City of Naples.

813 Wildwood LN, Naples

1035 3rd AVE S Unit 411, Naples
$2,457,000
3 Beds ⋅ 3 Baths ⋅ 226036778 MLS ⋅ Naples Square BLDG.
LUXURY CONDO IN THE HEART OF OLDE NAPLES — WALK TO BEACH, 5TH AVE & 3RD STREET SOUTH Experience the best of Naples living in this beautifully furnished, former model residence ideally located in the heart of Olde Naples, just a short stroll to the white-sand beaches, Fifth Avenue South, and Third Street South shopping and dining districts. This 3-bedroom + den, 3-bath former model condominium offers approximately 2,264 square feet of interior luxury living space, highlighted by designer furnishings, exquisite finishes, and meticulous attention to detail throughout. The open-concept floor plan features a spacious great room, gourmet kitchen with custom cabinetry, granite countertops, breakfast bar, and premium stainless-steel appliances. Expansive wraparound lanai provides seamless indoor-outdoor living with tranquil tropical views. The primary suite is a private retreat with a king bed, spa-like bath featuring dual vanities, soaking tub, and walk-in shower. Two guest suites, each with a queen bed and private bath, offer comfort and privacy for family or guests. The den provides flexible space for a home office, media room, or additional sleeping area. Enjoy secure ground-level parking and access to luxury community amenities including a club room with kitchen and lounge area, fitness center, resort-style pool and spa, and outdoor BBQ area perfect for entertaining. This residence combines the sophistication of designer living with the convenience of a premier downtown Naples location — all within walking distance to the beach, boating, fine dining, and entertainment that make Olde Naples one of Florida’s most coveted destinations.

1035 3rd AVE S Unit 411, Naples

13915 Old Coast RD Unit PH01, Naples
$6,595,000
4 Beds ⋅ 4 Baths ⋅ 226036789 MLS ⋅ Kalea Bay Tower 100 BLDG.
A rare opportunity to own an exceptional end-unit penthouse in Kalea Bay, one of Naples' most coveted waterfront communities. Perched atop Tower 100, PH01 offers breathtaking 270-degree panoramic views of the Gulf of Mexico, tranquil bays, Naples skyline, and Kinsale Golf Club, capturing spectacular sunrises and Gulf sunsets. Over $350,000 in architectural customizations completed during construction distinguish this residence. An expansive custom glass window frames unobstructed skyline, bay, and golf course views from the living room. The reimagined owner's suite features floor-to-ceiling sliding glass doors opening onto the outdoor terrace, while its redesigned spa-inspired bathroom offers the rare indulgence of Gulf views from the soaking tub and an oversized custom steam shower. Sophisticated interiors feature high ceilings, custom wood flooring, bespoke millwork, designer lighting, and cabinetry. Expansive glass doors open to a generous outdoor terrace, seamlessly blending indoor and outdoor living. The chef's kitchen boasts Wolf and Sub-Zero appliances, a natural gas cooktop, oversized island, and butler's pantry. Two guest suites feature private en-suite bathrooms, while a fourth bedroom or study offers access to a custom bathroom with shower. An exceptionally rare private, oversized, enclosed garage accommodates up to FOUR vehicles, a remarkable luxury in high-rise coastal living. Kalea Bay offers five-star resort amenities, including Tower 100's rooftop pool with panoramic views, barbecue and lounge areas, multiple resort pools, restaurants and bars, wellness center, tennis, pickleball, bocce, 12 guest cottages, beauty salon, kayak and paddleboard launches, and a vibrant social calendar. The optional Beach Club provides beachfront dining, beach chairs, umbrellas, towels, and food and beverage service directly on the sand. Gated entry and 24-hour security offer added privacy and peace of mind. PH01 combines extraordinary panoramic views, distinctive architectural customizations, exceptional privacy, and the ultimate Kalea Bay resort lifestyle.

13915 Old Coast RD Unit PH01, Naples

3971 Jasmine Lake CIR, Naples
$839,000
3 Beds ⋅ 2 Baths ⋅ 226036781 MLS
IMMEDIATE GOLF MEMBERSHIP INCLUDED - BEST VIEWS IN CYPRESS WOODS, LAKE VIEWS / SUNSET! AMAZING OPPORTUNITY!! FURNISHED - Single Family Home with 3 bedroom, 2 baths ~ Located in North Naples ~ Cypress Woods Golf and Country Club offers NEWLY RENOVATED GOLF COURSE, COMPLETED BY JANUARY 1, 2027 ~ 18-hole Gordon Lewis bundled golf ~ Spacious, upgraded, cove lighting, crown molding throughout, plantation shutters, ALL NEW porcelain flooring in bedrooms, King master suite with master bath has walk-in shower, large soaking tub, 2 vanities/his and her's, 2 NEW CUSTOM BUILT CLOSETS; 2 other Queen guest bedrooms, updated guest bath complete your new home in paradise! Home is situated on a premium lakefront lot with preferred Western exposure and tranquil lake/sunset views! Relax in the spacious, cozy living & dining areas that open directly into the screened in lanai area. Upgraded kitchen with breakfast bar is beautifully appointed with white custom paneled cabinetry with updated quartz counters, backsplash and Kitchen Aid stainless steel appliances, NEW A/C, Newer H20 heater, Newer LG washer/dryer, NEWER Custom Grill and beverage cooler on lanai. Enjoy your morning coffee or an evening cocktail with cross breezes from retractible screened front door/screened backyard and sunset on the lanai overlooking the serene lake or take an early morning swim or workout at the community facility with resort-style lifestyle ~ Professional pro shop, golf carts, driving range, putting green, fitness center, 8 NEW pickleball & tennis, 2 pools/food service, hot tub, NEW bocce pavilion! AWESOME UPDATED Clubhouse and Restaurants - formal dining, casual in the grille room, outside dining on the patio along golf course/lake, endless events & activities, book club, cards, mahjong, walking/bike trails, and more! Two car attached garage, hurricane shutters! Located just 20 mins from RSW/Airport, Downtown Naples, Shopping In Naples/Bonita Springs and mins to World Class Beaches ~ Cypress Wood Golf and Country Club Is Your Lifestyle Choice! UPDATED PHOTOS COMING THIS WEEK.

3971 Jasmine Lake CIR, Naples

9405 Whooping Crane WAY, Naples
$998,000
3 Beds ⋅ 2 Baths ⋅ 226035731 MLS
The stunning Summerwood floor plan, offers 3 Bedrooms PLUS a Den, 2 Bathrooms, 2-car garage, and POOL & SPA! The den can be used for an office, 4th bedroom, or TV/theater room. Positioned with a gorgeous view of the lake from the pool area, this exceptional residence welcomes you with impressive curb appeal and thoughtfully selected upgrades throughout, including a natural gas GENERATOR, for peace of mind. Located within the gated community of Greyhawk at Golf Club of the Everglades in North Naples, this home includes an open-concept great room, enhanced by soaring ceilings with an elegant coffered ceiling detail, creating an inviting atmosphere ideal for entertaining or relaxing at home. The gourmet kitchen stands out with stylish shaker cabinetry, beautiful hardware, quartz countertops, a decorative backsplash, and premium appliances, including a gas cooktop. Throughout the home, 1’ x 2’ tile flooring delivers a cohesive, upscale look with no carpet anywhere. Step through the zero-corner pocketing sliding glass doors to discover your own private outdoor retreat. The expansive covered lanai overlooks a custom swimming pool with a raised spa, creating the perfect setting for morning coffee, afternoon relaxation, or hosting family and friends. The OUTDOOR KITCHEN with gas grill is a major upgrade and perfect for entertaining. Additional highlights include upgraded bathroom finishes with quartz countertops, enhanced lighting and ceiling fans, a laundry room with cabinetry and sink, a huge covered front porch with ceiling fan, and attractive stone accents. Life at Greyhawk offers an exceptional collection of amenities, including clubhouse with social events, restaurants, a fitness center, tennis, pickleball, bocce, a resort-style pool, a tiki bar, and a dedicated social director. Social membership to the Golf Club of the Everglades with optional golf memberships available. Enjoy the convenience of a straight shot down Vanderbilt Beach Rd to Vanderbilt Beach and Mercato, and easy access to i-75. With its desirable location on the lake, upscale finishes, private pool and spa, and outstanding resort-style amenities, this home offers an incredible opportunity to enjoy the best of the North Naples lifestyle. Come experience the comfort, quality, and effortless Florida living that make this home truly special!

9405 Whooping Crane WAY, Naples

3200 Gulf Shore BLVD N Unit 107, Naples
$750,000
3 Beds ⋅ 2 Baths ⋅ 226026931 MLS ⋅ Coquina Club BLDG.
Steps from the beach, and steps from your own rented dock perfectly positioned along Doctor’s Bay, welcome to a rare waterfront retreat in the heart of The Moorings at the Coquina Club. This beautifully updated first-floor condo offers 3 bedrooms and 2 bathrooms, blending effortless, relaxed coastal charm with bespoke finishes and upscale appliances. This meticulously curated home is ready for you to enjoy Naples endless summer without delay. With views straight to the bay, you enter to a bright, open living space featuring crisp plank tile flooring throughout, a relaxed color palette, and abundant natural light. The pristine kitchen has been thoughtfully updated with clean white shaker cabinetry, sleek quartz countertops, and quality appliances. Both bathrooms feature timeless, clean finishes that continue the aesthetic. Three large bedrooms ensure enough space for family and guests, while the light and fresh color palette with the dappled sunlight that flows through the plantation shutters gives adds an unrivaled sense of space to the Florida coastal vibe. Coquina Club offers an ideal blend of amenities and location. Residents enjoy a bayside saltwater pool and grilling area, social room, showers, bike storage, and a vibrant sense of community. Boaters and water enthusiasts will love the 22 boat slips and kayak racks available for lease. Additional conveniences include a private storage unit and an assigned covered parking space. Perfectly situated across the street from the Vedado Beach access point, you’re just seconds from Venetian Village’s boutique shops and waterfront dining, and only three miles from the heart of downtown Naples, where world-class restaurants, galleries, and nightlife await. Whether you’re seeking a full-time residence or a seasonal retreat, this exceptional condo captures the very best of coastal living—offering unmatched location, beautiful design, and the confidence of extensive updates throughout the community. If you are looking for a renovation and months of dust, budget overruns and endless checks, this is not the home for you. Only buyers who wish to enjoy the beauty and exquisite lifestyle of downtown Naples immediately will be interested in this perfect property.

3200 Gulf Shore BLVD N Unit 107, Naples

6148 Rodney Bay LN, Naples
$2,390,000
3 Beds ⋅ 3.5 Baths ⋅ 226036746 MLS
Welcome to the Isles of Collier Preserve, where you will find yourself surrounded by natural beauty. There are over 1200 acres filled with biking and walking trails, waterways to kayak and beautiful vistas. This Stock Signature built home features a chefs' kitchen with gas cooking, a large island, plenty of cabinets and storage. There are 3 bedrooms, a private study, 3 full and one half bathrooms. The master suite offers 2 walk in closets, french doors to the lanai, a linen closet, a large bathroom with dual vanities, walk in shower and separate soaking tub. The Cambria III model features a much sought after 3 car garage. This home has added custom molding throughout, a coffered ceiling in the living area, decorator lighting, plantation shutters, and additional landscaping with outdoor lighting. The extra large lanai invites you to the Florida Lifestyle with an outdoor kitchen, large covered space for dining, entertaining or just relaxing. A gas heated pool and spa, all complemented by a custom wood paneled ceiling and Picture Window screens allow you to truly enjoy your outside space. Be as active as you would like in this amenity rich community. Enjoy the resort style pool, lap pool, both tennis and pickleball courts, and bocce. A fitness center and community center with classes, clubs, teams, and activities arranged by the on site activities director. Stop in the pool side Overlook Bar and Grill to catch your favorite football game or just to enjoy dinner with a water view. This gated community is nearby the Naples Botanical Garden, Hamilton Harbor Yacht Club, The Bayshore Arts District featuring coffee shops and restaurants. There is even a private pedestrian gate to enter the next door USOP National Pickleball Center with more than 50 courts. If you want to head out to Old Naples for dining, shopping or just a stroll on the beautiful beaches, you will find them less than 5 miles away. Professional Photos to follow soon.

6148 Rodney Bay LN, Naples

211 Flamingo AVE, Naples
$3,250,000
4 Beds ⋅ 3 Baths ⋅ 226036284 MLS
211 Flamingo Ave offers a substantial waterfront residence with an exceptionally spacious and functional floor plan, extensive recent upgrades and remodeling, and an outstanding location in the heart of Vanderbilt Beach. Set on an 80 by 121 foot Gulf access lot, the property is uniquely positioned with no homes directly across the canal, creating added privacy and a peaceful waterfront setting, along with some of the quickest Gulf access in Conners Vanderbilt Beach Estates. The home features 2,732 square feet of living area with four bedrooms, including one ideally suited as a private office or den with direct access from the primary suite, multiple living spaces, a pool and spa, and an oversized two car garage. The interior is open and bright, with a formal dining area, secondary family room, eight foot sliders and distinctive corner mitered windows. The updated kitchen features Bosch appliances, extensive cabinetry and storage, pantry space, and a built in wet bar with beverage cooler. A brand new additional freezer and ice maker have also been added in the garage. The primary suite stands out for its scale and unique layout, offering direct access to the office or den (4th BR), a large walk in closet with two entrances, a spacious bath with separate soaking tub and walk in shower, and direct access to the pool and lanai. A full bath is also accessible from the pool area while serving as a centrally located guest bath. The waterfront has recently undergone significant improvements with a new seawall and substantial dock system featuring a 20,000 pound boat lift plus a separate 7,000 pound lift with a beautiful Trex deck platform, ideal for an additional boat or personal watercraft. The pool and spa overlook the canal and are complemented by refreshed landscaping and Zoysia grass. Additional improvements include a tile roof completed in 2014. With generous interior space, substantial recent improvements, excellent boating infrastructure, added privacy and exceptionally convenient Gulf access, 211 Flamingo Ave offers a compelling waterfront opportunity in one of North Naples’ most desirable boating neighborhoods.

211 Flamingo AVE, Naples

1870 Ivory Cane PT, Naples
$999,000
5 Beds ⋅ 3 Baths ⋅ 226036761 MLS
NEW ROOF INSTALLED AS OF MARCH 16TH, 2026 with transferable warranty!!This rarely available five-bedroom, three-bath Emerald floor plan is tucked away on a quiet cul-de-sac in Saturnia Lakes, offering privacy and beautiful long lake views. The well-designed layout includes a three-car garage and an inviting outdoor living space with a pool and spa, ideal for both relaxing and entertaining. The custom outdoor kitchen features a Brand New grill and refrigerator, extending the home’s living space and making the most of Florida’s year-round lifestyle. Inside, the home showcases tile plank flooring throughout the main living areas, creating a cohesive and welcoming feel. The kitchen offers generous cabinetry, granite countertops, and ample prep space, complemented by an indoor wine refrigerator that adds both convenience and functionality. The living and dining areas flow seamlessly, making the home comfortable for everyday living and gatherings alike. Upstairs, a second-floor veranda provides an additional retreat with elevated views of the lake. The primary suite features custom closets and a private walk-out veranda overlooking the pool and water, offering a peaceful place to unwind. Saturnia Lakes delivers resort-style amenities, including multiple pools, a fitness center, yoga and dance studio, tennis courts, billiards, a playground, and a vibrant clubhouse. Located within top-rated school zones and just minutes from Naples’ white-sand beaches, exceptional dining, and premier shopping, this home offers both comfort and convenience. A beautifully maintained residence in a highly sought-after community, an opportunity worth seeing in person.

1870 Ivory Cane PT, Naples

2485 Crayton RD, Naples
$7,250,000
4 Beds ⋅ 5.5 Baths ⋅ 226036613 MLS
This Italian-inspired modern coastal residence sits on an oversized 0.40-acre lot in the heart of the Moorings community. Set at 12 feet of elevation, the home showcases refined European craftsmanship throughout. Porcelanosa is used for the flooring in all interior living spaces, the wall finishes and showers in every bathroom, and the outdoor kitchen backsplash. All cabinetry, including the kitchen and custom closet systems, was designed, built, and imported from Italy by Copatlife. The minimalist interior has no baseboards, crown molding, door frames, or traditional door hardware. Interior doors are Italian-made pivot doors by Ghizzi & Benatti, set flush into the walls with integrated hand-slot pulls, while the entry makes a statement with a show-stopping Andersen pivot door. The kitchen features Gaggenau appliances, including an integrated refrigerator and freezer, two full ovens plus a steam oven, and dual dishwashers, along with onyx countertops and a flush cooktop with a built-in pop-up downdraft ventilation system. Additional features include a full Lutron lighting system, a Pentair whole-home water filtration system, a 1,000-gallon propane tank, Andersen LiftSlide glass doors, and Andersen impact windows. Expansive indoor-outdoor living is complete with a custom pool, spa, sunken fire-pit, outdoor kitchen, and electric screens and shutters. This property is eligible for the private Moorings Beach Park.

2485 Crayton RD, 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.