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

8142 Lucello TER S, Naples
$1,029,000
3 Beds ⋅ 3 Baths ⋅ 226035667 MLS
Discover refined elegance and resort-style living in this beautifully appointed, turnkey-furnished Lazio residence in the prestigious gated community of Esplanade at Hacienda Lakes. Perfectly positioned on a premium preserve homesite with no neighbors behind, this three-bedroom-plus-den, three-bath home offers 2,356 square feet of sophisticated living space, extensive upgrades and exceptional indoor-outdoor entertaining areas. An upgraded full-lite glass entry door introduces an inviting interior featuring 10-foot ceilings, elegant tray ceiling details, 8-foot doors, crown molding and upgraded porcelain tile flooring throughout. The modified Lazio floor plan includes an expanded dining area, private den with doors and an open-concept design connecting the main living spaces. The gourmet kitchen showcases quartz countertops, upgraded 42-inch cabinetry, designer backsplash, pull-out drawers, under-cabinet LED lighting and premium Café appliances, including a 36-inch gas cooktop and built-in wall oven and microwave. The spacious primary suite offers an extended bay window sitting area, oversized walk-in closet and beautifully appointed bath with dual vanities, upgraded floor-to-ceiling shower tile, luxurious rain showerhead and frameless glass enclosure. Two additional guest bedrooms and baths provide comfortable accommodations with upgraded finishes and frameless shower enclosures. Designed for Southwest Florida's outdoor lifestyle, the expansive screened lanai overlooks a peaceful natural preserve, providing exceptional privacy. A custom heated saltwater pool with integrated raised spa, added in 2022, is complemented by an extended paver deck, creating an inviting setting for entertaining. The covered lanai can be enclosed with aluminum shutters for versatile indoor-outdoor living, while a private courtyard offers another tranquil retreat. Additional enhancements include a two-car garage extended four feet, Corefill block insulation, additional garage ceiling insulation, laundry sink, LED lighting in the primary suite and living area, personalized Vitex home technology system, security cameras and alarm system, smart and low-voltage wiring, floor outlets, upgraded interior paint and custom window treatments. Residents of Esplanade at Hacienda Lakes enjoy resort-style amenities including a clubhouse, resort and lap pools, fitness center, tennis, pickleball, bocce, dog park and full-time lifestyle director. Ideally located minutes from downtown Naples, Fifth Avenue South, Gulf beaches and Marco Island, this exceptional residence offers the perfect balance of luxury, privacy and convenience. Completed in June 2022, this thoughtfully upgraded home presents an outstanding opportunity to experience the best of Naples living.

8142 Lucello TER S, Naples

205 Park Shore DR Unit 4-413, Naples
$1,395,000
2 Beds ⋅ 2 Baths ⋅ 226033925 MLS ⋅ Park Shore Landings BLDG.
Enjoy breathtaking views of Venetian Bay from this beautifully maintained residence in Park Shore Landings. Spanning 1,753 square feet, this 2-bedroom plus den, 2-bath home offers an open-concept design that seamlessly connects the kitchen, dining, living, and lanai areas, creating an inviting setting for everyday living and effortless entertaining. The expansive west-facing lanai frames stunning sunsets and refreshing Gulf breezes, while abundant natural light enhances the warm and welcoming ambiance throughout. The primary suite is a serene retreat with a walk-in closet, dual sinks, and a walk-in shower. The kitchen features custom cabinetry, granite countertops, and a charming breakfast nook, striking the perfect balance of style and functionality. Additional highlights include impact-resistant windows, a comfortable den, a deeded covered parking space, and extra storage. Park Shore Landings offers exceptional amenities including a pool, spa, social room, library, and kayak storage and launch facilities. The community’s commitment to excellence is reflected in recent improvements, such as the 2022 reconstruction of the boardwalk, seawall, and 36 boat docks. Residents also enjoy access to a guest suite that may be reserved for visiting guests. Perfectly positioned just steps from Venetian Village and minutes from Waterside Shops, Artis-Naples, Mercato, and the renowned dining and shopping of 5th Avenue South and 3rd Street South, this residence provides an unmatched blend of coastal tranquility and vibrant urban convenience. Owners also have the exclusive opportunity to join the private Park Shore Beach, completing the quintessential Naples lifestyle.

205 Park Shore DR Unit 4-413, Naples

2905 Gulf Shore BLVD N Unit 803, Naples
$2,875,000
3 Beds ⋅ 3 Baths ⋅ 226034261 MLS ⋅ Westgate BLDG.
Enjoy sweeping Gulf views and gentle coastal breezes from this beautifully appointed top floor residence at Westgate in The Moorings. Offering three bedrooms, three bathrooms, and 2,805 square feet of living space, this inviting coastal retreat combines generous proportions with custom finishes throughout. The spacious great room provides a welcoming setting for everyday living and entertaining, framed by views of the Gulf and spectacular sunsets. A formal dining room, an open-air covered balcony, and a newly updated kitchen with high-end appliances further enhance the residence’s appeal. The primary suite features two walk-in closets and a well-appointed bath with dual sinks and a spacious walk-in shower, while both guest bedrooms offer comfortable accommodations and en-suite bathrooms. Additional features include impact-resistant windows, electric hurricane shutters, window treatments, a deeded covered parking space, and private storage. With just 48 residences and a beautifully remodeled lobby, Westgate offers an intimate beachfront setting complemented by a saltwater pool, sunset terrace, poolside social room, fitness center, bike and kayak storage, outdoor barbecue area, car wash, and professional on-site management. Direct beach access and proximity to the waterfront boutiques and restaurants of Venetian Village complete this exceptional Naples coastal lifestyle.

2905 Gulf Shore BLVD N Unit 803, Naples

1060 Borghese LN Unit 2006, Naples
$799,000
3 Beds ⋅ 3.5 Baths ⋅ 226038282 MLS ⋅ Aversana BLDG.
Experience elevated living at Hammock Bay in this exceptional 20th-floor residence, ideally positioned on the 20th floor of the building’s 21 stories. One of the limited floor plans offering higher ceilings than most residences, this three-bedroom, three-and-a-half-bath home combines a sense of spaciousness with breathtaking views of Marco Island, the surrounding mangroves, and spectacular Southwest Florida sunsets. Warm-toned marble flooring adds timeless elegance, while a formal dining room provides an inviting setting for entertaining. Each bedroom features lanai access, creating a seamless connection to the outdoors and offering a peaceful place to take in the stunning natural surroundings from this impressive vantage point. Hammock Bay offers a lifestyle centered around relaxation, recreation, and connection, with an array of amenities including a resort-style pool, fitness center, sauna, and hotel-style guest accommodations for visiting family and friends. An active social atmosphere offers opportunities to connect with neighbors and enjoy the community, while still allowing residents to embrace their own pace of living. Adding to the appeal, the building maintains a healthy reserve balance and has completed its required inspections, providing additional peace of mind for prospective buyers. With its elevated position, sought-after higher ceilings, elegant finishes, captivating sunset views, and exceptional community amenities, this residence presents a wonderful opportunity to enjoy the very best of Hammock Bay and the Marco Island & Naples lifestyles.

1060 Borghese LN Unit 2006, Naples

12444 Violet LN, Naples
$825,000
3 Beds ⋅ 3 Baths ⋅ 226037038 MLS
Discover an exceptional opportunity in Valencia Trails, where an oversized homesite, tranquil preserve views, and an ideal location set this beautifully appointed 2024-built "Pelican" model apart. Ideally situated to provide additional separation from neighboring homes on one side, this property offers a rare sense of space and privacy, with a lush wooded preserve as its backdrop. The desirable eastern exposure welcomes beautiful morning sunlight, while the expansive backyard offers ample room to add a custom pool and create your own private outdoor oasis. Inside, this thoughtfully designed home features 3 bedrooms, 3 full bathrooms, a versatile den with elegant French doors, and an attached 2-car garage. The gourmet kitchen is beautifully equipped with stainless steel appliances, a gas cooktop, quartz countertops, soft-close cabinetry, and a spacious walk-in pantry. Additional upgrades include impact-resistant windows and a picture-frame screened lanai that maximizes the peaceful preserve views. A well-placed home that makes coming and going a breeze, with the community’s new residents-only entrance or exit nearby. Valencia Trails is a premier 55+ community offering an extraordinary resort-style lifestyle. The spectacular 43,000-square-foot clubhouse features a resort-style pool, spa, restaurant, poolside bar, and an impressive selection of social and recreational amenities. Residents enjoy tennis, pickleball, a state-of-the-art fitness center, lap and resistance pools, scenic walking trails, two dog parks, and a vibrant calendar of activities. Combining a premium homesite, newer construction, and exceptional community amenities, this residence offers a wonderful opportunity to enjoy the best of Southwest Florida living.

12444 Violet LN, Naples

1287 Grand Canal DR, Naples
$2,049,000
3 Beds ⋅ 2 Baths ⋅ 226038004 MLS
One or more photo(s) has been virtually staged, AI generated or rendered. Discover the essence of Southwest Florida's coastal lifestyle in this beautifully designed Key West inspired waterfront residence, situated west of US-41 in the desirable Gulf Harbor community of Naples. Offering 3 bedrooms, 2 bathrooms, elevator, open concept kitchen, private boat dock, boat lift and picturesque canal views this property offers an opportunity to enjoy waterfront living with no HOA. Thoughtfully designed to capture the charm of coastal architecture this residence offers a distinctive floor plan highlighted by an upper-level primary suite, the only bedroom on its floor, creating a private retreat from the main living areas. With desirable western exposure, the primary suite provides a spectacular vantage point for breathtaking Naples sunsets and tranquil waterfront views. Boating enthusiasts will appreciate the private dock, and boat lift, providing convenient access to nearby Delnor-Wiggins Pass State Park and Bonita's Barefoot Beach, creating opportunities to enjoy boating, fishing and exploring Southwest Florida's coastline. Adding a thoughtful layer of storm preparedness, the property is equipped with a removable 4-foot barrier fencing system that can be installed when needed to help mitigate potential floodwater intrusion. Beyond its exceptional boating amenities this residence conveniently located near Naples' luxury shopping, fine dining, and world class entertainment. From leisurely afternoons on the water to elegant evenings at nearby restaurants, everyday offers an opportunity to experience the very best of Florida coastal living

1287 Grand Canal DR, Naples

7058 Barrington CIR Unit 102, Naples
$779,000
3 Beds ⋅ 2 Baths ⋅ 226038053 MLS ⋅ Barrington Club BLDG.
Discover exceptional value in Pelican Bay! This beautifully updated 3 bedroom, 2 bath first floor villa offers the convenience of no stairs, an attached garage, and a highly desirable X flood zone at an attractive price point. Located in one of Pelican Bay’s highest elevations, this meticulously maintained residence features an inviting blend of style, comfort, and functionality. The updated interior showcases luxury vinyl plank flooring in the guest bedroom and second bedroom/office, elegant plantation shutters throughout, crown molding, granite countertops, and stainless steel appliances, including a double oven. The spacious primary suite features newer tile flooring and a beautifully finished bath with marble inspired details, while custom built-ins in the closets and bedrooms provide thoughtful storage. Relax in the glass enclosed lanai, complete with impact resistant sliders and tranquil water views that set the stage for beautiful Southwest Florida sunsets. Enjoy Pelican Bay’s renowned lifestyle, including private Gulf front beach access, resident tram service, and beachfront dining and entertainment. Additional highlights include newer roofs fully paid for by the association and an HOA that covers landscaping, water, sewer, cable, internet, and more. With most furnishings negotiable, the home has been lovingly maintained and occupied only approximately five months each year. Conveniently located near Mercato, Waterside Shops, Artis—Naples, and an outstanding selection of dining and shopping, this is an opportunity to enjoy the best of Naples coastal living in one of its most sought after communities.

7058 Barrington CIR Unit 102, Naples

565 CORAL DR, Naples
$3,150,000
4 Beds ⋅ 3.5 Baths ⋅ 226036740 MLS
An extraordinary opportunity awaits in the heart of prestigious Coquina Sands, where an estate-sized homesite, exceptional outdoor amenities and an enviable location create endless possibilities for the discerning buyer. Offered at nearly land value, this remarkable property presents the rare flexibility to enjoy the existing residence, thoughtfully reimagine its interiors or create an entirely new custom estate in one of Naples' most desirable coastal neighborhoods. Particularly compelling is the property's impressive building potential, with a building footprint exceeding 8,000 square feet, providing an exceptional canvas for a magnificent new luxury residence. The existing home features a bright, generously proportioned open floor plan with four bedrooms, a versatile den easily accommodating a fifth bedroom, and an abundance of inviting spaces designed for both everyday comfort and entertaining. The true centerpiece of the property is its spectacular outdoor living environment, where an inviting pool and spa are complemented by a dedicated entertainment pavilion featuring a summer kitchen and outdoor living room. This impressive setting provides the perfect backdrop for elegant gatherings, relaxed afternoons and year-round enjoyment of Naples' exceptional climate. A new roof installed in 2024 adds significant value to the existing residence. Equally compelling is the property's premier location, just minutes from the sugar-sand beaches of Lowdermilk Park, The Moorings Golf and Country Club, the highly anticipated Naples Beach Club Four Seasons Resort, and the celebrated shopping, dining and entertainment of Fifth Avenue South. Whether envisioned as a sophisticated coastal retreat, a substantial renovation opportunity or the future site of a magnificent new luxury estate, this exceptional Coquina Sands offering combines immediate enjoyment with outstanding long-term potential in a highly coveted Naples setting.

565 CORAL DR, Naples

2299 Somerset PL, Naples
$1,650,000
3 Beds ⋅ 4 Baths ⋅ 226037471 MLS
Discover exceptional indoor-outdoor living in this beautifully appointed WCI Laurel model, the largest floor plan available in LaMorada. Offering three bedrooms plus a den, four full bathrooms, and a spacious upstairs bonus room, this residence combines thoughtful upgrades, inviting entertaining spaces, and practical storm protection for an elevated Southwest Florida living experience. Entering through the elegant iron front entry door into the main living areas feature a recently upgraded kitchen with substantial quartz countertops, a gas range, and attractive cabinetry. Personalized touches in lighting, accent walls, and a custom-built entertainment center add unique touches throughout the interior, while the versatile floor plan offers plenty of room for everyday living, working from home, and hosting family and friends. Outdoor living takes center stage on the expansive covered lanai, where a distinctive wood-plank ceiling adds warmth and character. The resort-style heated saltwater pool & spa provide a relaxing backdrop, while the outdoor kitchen and TV make it easy to enjoy meals, watch a game, or spend time with guests. Hurricane shutters enclose the entire covered portion of the lanai, providing added protection when needed. Upstairs, the large bonus room offers exceptional flexibility, with a full wet bar, full bathroom, walk-in closet, and balcony. The generous space can accommodate a media area, billiards & game room, fitness space, or comfortable guest retreat. Additional features include a three-car garage, whole-home generator, tankless water heater, and impact windows & doors. With its versatile layout, luxury interior details, inviting outdoor living area, and practical protective features, this LaMorada home offers a highly desired combination of comfort, functionality, and entertaining potential.

2299 Somerset PL, Naples

2140 Harlans RUN, Naples
$1,250,000
3 Beds ⋅ 2 Baths ⋅ 226038220 MLS
Exquisite Fully Remodeled Hawksridge Pool Home! Beautifully updated 3-bedroom plus den, 2-bath residence offering 2,229 square feet of living space in highly sought-after Hawksridge. French door entry opens to an airy layout with vaulted ceilings and modern porcelain tile flooring throughout. Spacious living and dining areas flow seamlessly to the screened lanai and pool, creating an easy transition between indoor and outdoor living. A gourmet kitchen features quartz countertops, stainless steel appliances, wine cellar, subway tile backsplash, abundant cabinetry, and a large peninsula with seating. The primary suite offers private access to the lanai, a generous walk-in closet, and a remodeled bathroom with dual sinks, a walk-in shower and a soaking tub. Outdoor living space includes an expansive screened lanai, sparkling pool, outdoor shower, and multiple seating areas for dining or relaxation. Situated on an oversized .59-acre lot with mature landscaping, the property offers exceptional privacy and curb appeal. Hawksridge is an established gated community known for low quarterly HOA fees, a clubhouse, fitness center, and tennis courts. Located just minutes from Naples beaches, shopping, fine dining, and entertainment, this home delivers both convenience and comfort. Move-in ready and fully remodeled, this property combines quality finishes, an open layout, and a premium central Naples location within a well-maintained community, perfect for buyers seeking a modern home with space, style, and privacy in a prime setting.

2140 Harlans RUN, 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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