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

36 Las Brisas WAY Unit 37, Naples
$5,250,000
3 Beds ⋅ 3.5 Baths ⋅ 226028455 MLS
Introducing 36 Las Brisas. Extraordinary, effortless living beyond compare. Completely redesigned by Stofft Cooney Architects, Knauf-Koenig Group and Calusa Bay Design, this developer’s personal residence is a singular expression of refined luxury. Every finish and detail has been thoughtfully curated to create a one-of-a-kind home of exceptional beauty, sophistication and ease. Soaring vaulted ceilings, floor-to-ceiling impact glass, exquisite custom millwork and striking architectural detailing define the interiors. Designer wallcoverings, custom window treatments, hand-knotted rugs, wide plank European oak floors, stunning layered furnishings and an exceptional interior and exterior lighting package elevate every space. State-of-the-art control4 technology seamlessly integrates lighting, security, access and sound, with intuitive controls and remote access for effortless management from anywhere. The chef’s kitchen features separate working and seating islands, Wolf and Sub-Zero appliances, a full-size wine refrigerator and extensive custom cabinetry. Three beautifully appointed en-suite bedrooms, 3½ baths and an oversized two-car garage complete this impeccably finished, fully furnished residence. Beyond the walls of glass, a spectacular landscaped and securely gated courtyard creates a private resort-like retreat. Lush tropical gardens, an inviting plunge pool and gracious outdoor living spaces provide an enchanting setting for entertaining or quiet relaxation, seamlessly blending indoor and outdoor living. The villa’s one-of-a-kind design reflects exceptional craftsmanship and thoughtful planning. Natural light illuminates rich textures and finishes, while the open, airy layout balances gracious entertaining with tranquil private retreats. Every space has been designed to be as functional as it is beautiful. In the heart of Pelican Bay, residents enjoy three miles of deeded beachfront, oceanfront dining, extensive tennis and pickleball programs, and exceptional recreational amenities. Located within walking distance to Waterside Shoppes offering world class shopping and dining, Artis Naples, the beach, and minutes from Mercato and Fifth Avenue. With a virtually maintenance-free exterior, this is Naples living at its most refined. A rare opportunity to own a turnkey, designer-furnished residence with the quality and character of a custom estate, paired with the ease of a more intimate footprint. The signature Calusa Bay experience, without compromise. An exceptional Naples address.

36 Las Brisas WAY Unit 37, Naples

5190 Teak Wood DR, Naples
$3,999,000
6 Beds ⋅ 7.5 Baths ⋅ 226036023 MLS
A rare opportunity to own an impressive private estate in sought-after Logan Woods! Situated on over 2.5 acres, this expansive residence, built in 2009, offers 7,639 square feet under air and 11,568 total square feet, providing extraordinary space, privacy, and versatility. An impressive foyer welcomes you into generously proportioned living spaces designed for both grand entertaining and comfortable everyday living. The spacious primary suite features a sitting area, oversized bathroom, and expansive dressing area, creating a private retreat. The well-appointed, catering-size kitchen boasts top-of-the-line appliances, a wine cooler, and ice maker, complemented by a dedicated wine room. A formal living room and dining room provide elegant entertaining spaces, with a see-through fireplace connecting the formal dining room and kitchen. With 6 or more bedrooms and 8 bathrooms, including 6 full baths and 2 half baths, this estate offers exceptional accommodations for family, guests, and multigenerational living. Additional highlights include a huge upstairs balcony overlooking the back yard, a dedicated home office, and a loft above one of the two-car garages, offering flexibility for a variety of lifestyle needs. Step outside to your own private resort-style setting featuring a pool and spa, beautifully landscaped grounds, and gated entry. The expansive property offers a unique combination of space, privacy, and possibilities rarely found so close to Naples' premier shopping, dining, and Gulf beaches. Conveniently located near Waterside Shops, Mercato, Fifth Avenue South, and the Gulf beaches, with easy access to Southwest Florida International Airport, this remarkable Logan Woods estate presents an exceptional opportunity to enjoy spacious estate living in a desirable Naples location.

5190 Teak Wood DR, Naples

7319 Lantana CIR, Naples
$995,000
3 Beds ⋅ 2 Baths ⋅ 226037647 MLS
Discover the art of exceptional living in Olde Cypress! As one of North Naples most-sought after communities, Olde Cypress offers brilliantly remastered Clubhouse with casual and fine dining, championship golf, tennis and pickle ball, bocce courts, pool, fitness center, a vibrant social calendar and a wonderful sense of community, where you instantly belong. Just beyond the community, the very best of Naples living awaits, with world-famous beaches, water sports and boating, nature trails, upscale shopping and dining, art galleries and so much more. Within the community, tucked away amid lush tropical greenery on a peaceful, private lot, this tastefully REFRESHED, move-in ready STOCK Development residence delivers a lifestyle that defines relaxed luxury and offers a perfect balance for indoor/outdoor living. With 3 bedrooms, 2 bathrooms and an oversized 2-car garage, the home also features the following UPGRADES: custom cabinetry, high-end CAFE appliances, exquisite CASHMERE TAJ MAHAL quartzite counter-tops in kitchen and bathrooms, soft color palette, DESIGNER lighting and mirrors, elegant tile flooring and crown molding in living areas, accent wall, hardwood floors in all bedrooms, vaulted ceilings, plantation shutters, hurricane IMPACT glass sliders, windows and doors, and a KOHLER GENERATOR for your peace of mind. As you step outside, a recently REFRESHED, screened-in patio with sparkling HEATED POOL and SPA is a natural extension of the home and an invitation to slow down. A peaceful Naples retreat to call your own. An exceptional lifestyle just outside your door. Welcome home.

7319 Lantana CIR, Naples

1925 Metropolitan BLVD Unit 1204, Naples
$5,100,000
4 Beds ⋅ 4.5 Baths ⋅ 226036189 MLS ⋅ Avra BLDG.
One or more photo(s) has been virtually staged, AI generated or rendered. MOVE-IN READY Q4 2026. A rare opportunity to experience AVRA at Metropolitan Naples beyond the renderings. Residence 04 is nearing completion and has been professionally photographed, offering an authentic first look at the finished interiors, sweeping views, and exceptional scale of this private residence. Set within an exclusive collection of only 56 residences, this four-bedroom, four-and-one-half-bath home encompasses 3,351 square feet of air-conditioned living space and a 549-square-foot terrace, totaling 3,900 square feet of refined indoor and outdoor living. Panoramic views spanning Naples Bay, downtown Naples, and the Gulf provide an extraordinary backdrop, culminating in spectacular western sunsets from the expansive wraparound terrace. The thoughtfully composed split floor plan balances gracious entertaining with privacy, featuring a generous Great Room, private VIP guest suite, and a separate terrace adjoining the owner’s suite. Floor-to-ceiling impact glass frames the surrounding landscape and creates a seamless connection between the interiors and outdoor living spaces. Sophisticated finishes include elegant tile flooring, premium Italian cabinetry, and a chef-inspired kitchen appointed with Wolf and Sub-Zero appliances. Outdoors, a private BBQ grill and integrated wet bar transform the terrace into an extension of the residence, equally suited for intimate evenings or entertaining against the Naples skyline. AVRA presents an elevated collection of private amenities, anchored by a 15th-floor infinity-edge pool, outdoor bar, and social deck overlooking Naples Bay, downtown, and the Gulf. Residents also enjoy a state-of-the-art fitness and yoga center, 24/7 on site concierge, private shuttle service to downtown and the beach, resident lounge with bar and catering kitchen, luxury guest suite, business and conference center, owner’s lounge, putting green, outdoor spa, fire-table seating, BBQ stations, and lush subtropical landscaping. Positioned within Metropolitan Naples, AVRA places 5th Avenue South, Bayfront, Naples Bay, acclaimed dining and shopping, and Naples’ renowned white-sand beaches within minutes. With only 56 residences, AVRA offers a level of privacy and exclusivity rarely found this close to downtown, pairing the intimacy of boutique condominium living with one of Naples’ most desirable locations. Residence 04 is scheduled for completion in Q4 2026. Current photography showcases the actual residence and its progress rather than developer renderings.

1925 Metropolitan BLVD Unit 1204, Naples

591 93rd AVE N, Naples
$2,595,000
4 Beds ⋅ 4.5 Baths ⋅ 226037368 MLS
Experience the pinnacle of coastal sophistication in this 2022-built masterpiece located in the highly sought-after enclave of Naples Park. Spanning 3,100 square feet of refined interior living space, this residence seamlessly blends high-design aesthetics with unparalleled structural integrity. Unlike standard builds, this home features a precast concrete floor and a concrete topping slab on the second level—a significant engineering upgrade that ensures lasting durability and a solid feel throughout. The heart of the home is a sprawling chef’s kitchen, meticulously designed for both grand entertaining and intimate daily life. The thoughtful layout places the primary suite on the first floor, offering a private retreat with effortless access to the main living areas. Upstairs, you’ll find a spacious loft that opens to its own balcony, creating a versatile second living space bathed in Florida sunlight. With four bedrooms with ensuite bathrooms and a half designer bathrooms, the scale of this home is truly impressive. Indoor-outdoor living is perfected here. The living area opens directly to a stunning pool lanai area, allowing you to step right out into your private oasis. This outdoor retreat features a heated pool for year-round enjoyment and a spacious, covered seating area complete with a flat-screen TV—ideal for lounging in the shade while keeping an eye on the game. For additional outdoor versatility, the rear of the home offers a separate space tucked away from the immediate pool area, providing a distinct spot for gardening, play equipment or quiet relaxation. Peace of mind is built into every detail, from the impact glass on all windows and doors to the efficiency of a two-zone air conditioning system. Life in Naples Park offers a unique sense of freedom with no HOA fees and an unbeatable location. Located in the coveted and much desired 500 block of Naples Park, enjoy the coastal lifestyle with a quick bike ride to the white sands of the Gulf, or explore the world-class shopping and dining at Mercato and the prestigious Ritz-Carlton Resort nearby. When you crave the historic charm of downtown, the vibrant energy of 5th Avenue South is just a short drive away. This is more than a home; it’s a sophisticated gateway to the very best of North Naples.

591 93rd AVE N, Naples

9021 Sorreno CT, Naples
$3,295,000
5 Beds ⋅ 5.5 Baths ⋅ 226037190 MLS
FULL GOLF MEMBERSHIP INCLUDED! A RARE FIND with room for the whole family! Experience an exceptional blend of luxury, space, and resort-style living in this rarely available, two-story Mercede floor plan, ideally situated within the highly sought-after Esplanade Golf & Country Club of Naples. Built in 2018, this impressive residence offers 4,813 square feet of beautifully appointed living space and 6,449 total square feet under roof, featuring five spacious bedrooms (each with their own private ensuite bath), den, first floor bonus room, versatile upstairs loft, and five and a half baths. Perfectly positioned to capture expansive lake views and sweeping vistas of the 11th fairway, this extraordinary home offers an exceptional combination of sophisticated design, functionality, and an unbeatable location. The expansive interior showcases upgraded wood-look tile flooring throughout the main living areas, complemented by plantation shutters on every window, freshly painted interior, and brand-new carpeting. Additional enhancements include hurricane-impact windows and doors, insulated interior walls for enhanced comfort and energy efficiency, a three-zone air-conditioning system, and brand-new custom built-in closet systems in the primary suite. A freshly painted exterior, newly installed garage epoxy flooring, and refreshed landscaping in both the front and rear further elevate this meticulously updated residence. Step outside to your own private tropical retreat, where a gas-heated swimming pool and spa with a sun shelf invite you to relax. One of this home's most desirable attributes is its prime location just steps from the convenient walking path leading directly to Esplanade's spectacular amenity campus. Located just across the street and one home to the right, this nearby access provides exceptional convenience to the community's vibrant resort-style lifestyle without the need to drive. This extraordinary home offers the perfect balance of elegance, comfort, and resort-style living—enhanced by the included full golf membership in one of Naples’ most coveted communities. Esplanade Golf & Country Club of North Naples offers a true “Lifestyle Community” with world-class amenities, including a resort pool with cabanas and the popular “Bahama Bar,” tennis, pickleball, bocce, a 14-mile network of bike/walking trails, and an 18-hole private golf course. The impressive 15,000 Sq Ft clubhouse features a restaurant, bar, wine-tasting room, wine lockers, and a Starbucks-style café. Best of all, the property’s landscaping, irrigation, golf membership, and all community amenities are covered under a quarterly fee of just $3,832—no additional fees or memberships required! Don't miss your opportunity to own this exceptional home in one of Naples’ most sought-after communities. COMING SOON: Fully renovated and expanded poolside Bahama Bar; expanded outdoor bar at the Barrel House; expanded golf practice range; and INDOOR PICKLEBALL COMPLEX!

9021 Sorreno CT, Naples

9194 Cayman DR, Naples
$849,000
3 Beds ⋅ 3 Baths ⋅ 226037689 MLS ⋅ Azure At Hacienda Lakes BLDG.
Built in 2023 and upgraded throughout, this exceptional 3-bedroom, 3-bath home offers modern luxury, thoughtful design, and outstanding value. The spacious floor plan includes a versatile second-floor loft/den— perfect for a home office, media room, or guest space—along with a 2-car attached garage. After purchase, the owners invested significantly to elevate the outdoor living experience, adding a stunning saltwater pool and spa with upgraded water features and premium stone tile. The entire area is enclosed by a top-of-the-line screened cage with “picture window” screens, creating a seamless, unobstructed view that truly sets this home apart. This residence is completely move-in ready—absolutely nothing to update or improve—and is priced well below the total amount invested, making it an incredible opportunity. Located in Azure at Hacienda Lakes, a newer, upscale gated community in South Naples developed by Toll Brothers, residents enjoy a resort-style lifestyle with world-class amenities. The community features a beautifully appointed clubhouse with fitness center and social spaces, a resort-style pool and spa, tennis and pickleball courts, and scenic walking paths. Perfectly positioned just minutes from downtown Naples, you’ll have easy access to renowned 5th Avenue dining and shopping, the area’s pristine Gulf beaches, and nearby Marco Island. With convenient access to I-75, everything you need is close by while still enjoying the privacy of a gated community. This is the deal you’ve been waiting for—don’t miss this rare opportunity to own a like-new, highly upgraded home in one of Naples’ most desirable communities!

9194 Cayman DR, 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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