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

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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

3377 Gulf Shore BLVD N Unit 4D, Naples
$2,350,000
3 Beds ⋅ 3 Baths ⋅ 226037103 MLS ⋅ Waldorf BLDG.
Enjoy captivating Gulf views and spectacular sunsets from this beautifully appointed fourth-floor residence at The Waldorf in The Moorings. Offering three bedrooms, three bathrooms, and 2,937 square feet of living space, this inviting beachfront retreat combines generous proportions with timeless finishes throughout. The expansive living room provides a welcoming setting for everyday living and entertaining, with broad windows framing white sand, swaying palms, and the Gulf beyond. An adjoining enclosed beachfront lanai offers space for casual dining and relaxing with the water in view, while a separate formal dining room and wet bar further enhance the residence’s appeal. The thoughtfully designed kitchen features white cabinetry, granite countertops, and stainless steel appliances. The spacious primary suite opens to a sitting area framed by custom built-ins and views across the bay, complemented by a generous walk-in closet and an adjoining bath with dual sinks, a dedicated vanity, and an oversized walk-in shower. The comfortable guest bedrooms provide flexibility for visiting guests, a home office, or a quiet retreat. Crown molding, plantation shutters, and impact glass on the west-facing windows and sliders add to the home’s appeal. Additional features include a deeded under-building parking space and ample storage. Residents of The Waldorf enjoy direct beach access, a beachfront pool, fitness center, and a Gulf-front deck with a fire pit and inviting seating areas. Nearby, the waterfront boutiques and restaurants of Venetian Village complete this exceptional Naples coastal lifestyle.

3377 Gulf Shore BLVD N Unit 4D, Naples

3070 Gulf Shore BLVD N Unit 105, Naples
$825,000
2 Beds ⋅ 2 Baths ⋅ 226038339 MLS ⋅ Holly Greens Villa BLDG.
Discover Holly Greens Villas, an enchanting villa-style community offering the privacy and feel of a single-family home. Showcasing the largest floor plan available in the community, this beautifully reimagined, fully renovated ground-floor residence features an abundance of natural light with windows on all four sides and the convenience of a covered carport located directly adjacent to the unit. Originally designed as a three-bedroom residence, the interior has been thoughtfully redesigned to create a modern floor plan featuring two spacious bedrooms plus a versatile den, ideal for a home office, additional sleeping quarters, or flexible living space. Every detail has been carefully considered, blending sophisticated finishes, exceptional craftsmanship, and modern functionality. At the heart of the home is a stunning remodeled kitchen featuring custom cabinetry, generous pantry storage, elegant quartz countertops, and a premium stainless steel appliance package. Highlights include an induction cooktop, double convection ovens with microwave, and a beautifully designed layout that seamlessly connects the kitchen to the main living areas, creating an inviting space for everyday living. The spacious primary suite offers a peaceful retreat, complete with an oversized, custom walk-in closet by California Closets and a beautifully remodeled bathroom featuring quartz countertops and upscale finishes. The generously sized guest bedroom and additional renovated bathroom provide comfort and privacy for guests. Extensive renovations and upgrades include hurricane-impact windows and sliding glass doors throughout, new plumbing, updated electrical w/ upgraded 230-amp service, a new ac system, and a tankless water heater. Additional appointments include solid wood doors, recessed Lutron LED lighting, plantation shutters, electric privacy shades on sliding glass doors, and a full-size stackable LG w/d. The residence also features wiring in place for a future ev charging station! Holly Greens Villas offers an exceptional location surrounded by tree-lined streets, lush tropical landscaping, and some of Naples’ most prestigious waterfront residences. The pristine Gulf beaches are conveniently located within walking distance of the community, making it easy to enjoy leisurely beach walks, breathtaking sunsets, and the coastal lifestyle that makes Naples so desirable. Residents also have the opportunity to join the Moorings Property Owners Association, which provides access to the exclusive Moorings Beach Park, featuring private beach access and convenient parking. Just minutes from the renowned waterfront dining and shopping at Venetian Village, Waterside Shops, and the vibrant boutiques and restaurants of Fifth Avenue and Third Street South, this exceptional location places the very best of Naples at your fingertips. Experience the perfect combination of sophisticated, move-in-ready living, neighborhood charm, and an unbeatable coastal Naples location.

3070 Gulf Shore BLVD N Unit 105, Naples

2900 Gulf Shore BLVD N Unit 310, Naples
$875,000
3 Beds ⋅ 2 Baths ⋅ 226038325 MLS ⋅ Gulf Shore Subd BLDG.
**Water Views, Beach Access & Prime Naples Location!** Enjoy the best of the Naples waterfront lifestyle at this beautifully located residence at 2900 Gulf Shore Boulevard N, Unit 310. Ideally situated along prestigious Gulf Shore Boulevard, this inviting condo offers captivating views of Moorings Bay and is just approximately a quarter mile from beach access. Relax on the enclosed lanai or open the sliding doors to let in the coastal breeze while watching boats glide across the bay and dolphins pass by. The interior has been enhanced with **updated flooring and doors**, adding a refreshed touch to the living space. Whether you're looking for a full-time residence, seasonal retreat, or investment opportunity, this property offers an exceptional location and the opportunity to enjoy the best of Southwest Florida living. The unit is now **priced to sell**, making this an opportunity worth exploring. Take advantage of the convenient walk to **Venetian Village**, known for its waterfront restaurants, boutique shopping, and scenic bayfront atmosphere. A short drive brings you to the vibrant dining, shopping, galleries, and entertainment of **Fifth Avenue South** and the charming boutiques of Third Street South. Nearby outdoor activities include beach walks, boating, paddleboarding, fishing, and exploring the beautiful Gulf Coast shoreline. For boating enthusiasts, there may also be an opportunity to rent a boat slip, subject to availability and community rules. Spend your days enjoying the beach, watching the activity on Moorings Bay, or exploring Naples by land and water. **Beautiful bay views, nearby beach access, updated interior features, and an outstanding Naples location make this a wonderful opportunity to embrace the coastal lifestyle.**

2900 Gulf Shore BLVD N Unit 310, Naples

9090 Cascada WAY Unit 202, Naples
$775,000
3 Beds ⋅ 3 Baths ⋅ 226037979 MLS ⋅ Cascada BLDG.
Your own private elevator. Sweeping golf course and lake views. Golden sunsets over the fairways. Coveted second-floor end residence. Over 3,000 square feet with three spacious bedrooms, a study and three full baths. Welcome to Cascada, one of the few double-gated neighborhoods in Fiddler’s Creek, where this inviting retreat places you very close to both the village pool and the community’s exceptional amenities. Begin the morning with coffee on the expansive screened lanai as the landscape comes to life, then return at day’s end to watch the northwest sky soften into sunset, overlooking the golf course. Arrive by private elevator or a dramatic staircase beneath a soaring 21-foot ceiling. Porcelain tile, crown molding, plantation shutters and softly backlit tray ceilings bring warmth and refinement to the main living spaces. Sliding glass doors open from the great room to the lanai, connecting relaxed gatherings indoors with tranquil views beyond. At the heart of the home, the kitchen pairs granite counters and quality wood cabinetry with a tile backsplash, under-cabinet lighting, a walk-in pantry and an inviting breakfast area. Stainless appliances include a natural gas range, built-in microwave, dishwasher and French-door refrigerator. Retreat to the primary suite, where private lanai access invites a quiet evening outdoors and two walk-in closets provide generous storage. The en-suite bath features dual granite vanities, a walk-in shower with dual showerheads and a bench, and a separate water closet with bidet. The suite’s in-ceiling speakers let you set the mood for unwinding after a day outdoors. Guests enjoy two spacious bedrooms, including an exceptionally large room that offers flexibility for two king beds and could serve as a second primary retreat. Porcelain tile, crown molding and plantation shutters carry the home’s refined finishes into the guest accommodations. Each guest bedroom has a private en-suite bath. French doors introduce the study, where wood-look porcelain tile and two impact-resistant windows create a welcoming workspace. A laundry room with cabinetry, sink, front-load washer and gas dryer adds convenience. On the lanai, porcelain tile, ceiling fans and mounted speakers set the scene for leisurely lunches and sunset conversations above the fairways and water. A two-car garage and speakers in select living spaces complete the residence. Fiddler’s Creek offers resort-style pools, fitness and spa facilities, six Har-Tru tennis courts, 10 pickleball courts, fine and casual dining, and an active calendar of social events and activities. Miles of tree-lined sidewalks invite morning walks, evening strolls and an active outdoor lifestyle. Optional golf and beach memberships at The Creek Course and Tarpon Club complement a prime location near Old Naples and Marco Island’s beaches, shopping and dining.

9090 Cascada WAY Unit 202, Naples

2850 Gulf Shore BLVD N Unit 106, Naples
$899,900
2 Beds ⋅ 2 Baths ⋅ 226038595 MLS ⋅ Jennifer Shores BLDG.
Experience breathtaking panoramic views of Moorings Bay from this beautifully reimagined and meticulously redesigned condominium. Every detail has been thoughtfully curated, blending modern elegance with coastal charm to create a truly exceptional living space. The open-concept layout is enhanced by premium wood flooring, offering durability and sophisticated style. At the heart of the home, the custom-designed kitchen showcases new Samsung appliances, sleek quartz countertops and refined finishes, ideal for everyday living and entertaining. The expansive living area is framed by oversized sliding impact glass doors that flood the space with natural light and open seamlessly to stunning bay and pool views, creating a harmonious indoor-outdoor lifestyle. The redefined living and dining area is further elevated by a built-in bar complete with a wine and beverage cooler, ideal for hosting guests. Both bedrooms are generously proportioned, with the primary suite featuring a spacious walk-in closet. The two beautifully appointed baths boast designer fixtures, luxury tile and high-end finishes. Additional conveniences include a dedicated laundry area and assigned parking. Within Jennifer Shores, a rare pet-friendly community allowing up to two pets up to 160 pounds. Residents enjoy a relaxed yet upscale coastal lifestyle. Boat slips are available for lease, and Moorings Bay provides direct, bridge-free access to the Gulf, ideal for boating enthusiasts. Owners benefit from flexible leasing options, with ability to rent their unit twice annually with a 30-day minimum. This exclusive, low-density building consists of just 32 residences and is ideally on Gulf Shore Boulevard North, just north of Doctor’s Pass and south of Harbour Drive. Enjoy the best of Naples living with beach access across the street, inviting you to spend your days soaking up the sun and sea breeze. A short bike ride brings you to the upscale shops and dining of Venetian Village. Within the community, residents can unwind at the bayfront pool, relax on the fishing pier or gather at the grilling area, all set against the tranquil backdrop of Moorings Bay. This is coastal living at its finest, where luxury, comfort and location come together seamlessly.

2850 Gulf Shore BLVD N Unit 106, Naples

3410 Runaway CT, Naples
$2,295,000
3 Beds ⋅ 3 Baths ⋅ 226035234 MLS
Beautifully appointed and meticulously maintained, this furnished residence offers refined interiors, extensive upgrades, and a coveted FULL GOLF MEMBERSHIP AT THE MEMBERS CLUB AT MARCO, with golf at The Rookery and Hammock Bay and access to the JW Marriott Beach Club on Marco Island. Situated on a premium oversized cul-de-sac lot, the home enjoys exceptional privacy and spectacular lake views of the 10th hole of Fiddlers Creek golf—a setting that stands apart even among higher-priced new construction in Fiddler's Creek. The open floor plan features three en-suite bedrooms, a den, and a three-car garage. Interior details include chiseled-edge marble flooring, designer furnishings, plantation shutters, custom window treatments, crown molding, and tray and coffered ceilings. The updated kitchen offers Cambria quartz countertops and backsplash, new GE appliances, additional cabinetry, and a custom pantry. The formal dining room includes a bar with a Uline 28-bottle wine refrigerator. The den features a coffered ceiling, built-in bookcase, credenza, rich wood flooring, and a California Closet system with a safe. The owner's retreat includes a seating area, new flooring, designer window treatments, lanai access, and two walk-in closets. The primary bath offers marble tile, dual sinks, a soaking tub, and a walk-in shower. Two guest suites feature private baths and California Closets, with one bath providing lanai access. The extended lanai showcases lake and golf views, a saltwater pool and spa with a water feature, updated bar seating six, and an outdoor kitchen with a grill, hood, and refrigerator. Outdoor dining, two televisions, and decorative landscape lighting complete this inviting entertaining space. The air-conditioned three-car garage, the ultimate man-cave, includes Gladiator organization with a coordinating refrigerator, extensive shelving, ceiling fans, epoxy flooring, insulated doors, and insulated attic storage with pull-down stairs. Additional upgrades include a whole-house gas generator, tankless water heater, Sonos music system, security alarm, impact windows and doors, motorized hurricane shutters, and A/C replacements in 2024 and 2019. Fiddler's Creek is a distinguished, gated resort community where residents enjoy a 54,000-square-foot Club & Spa, resort-style swimming pools, fitness facilities, spa services, tennis, pickleball, bocce, casual and fine dining, and an active social calendar. Ideally located between downtown Naples and Marco Island, the community offers convenient access to the Gulf beaches, boating, shopping, and the renowned restaurants and boutiques of Fifth Avenue South. The transferable full golf membership to The Members Club at Marco offers privileges at The Rookery and Hammock Bay, plus access to the private JW Marriott Marco Island beach club. A rare opportunity to enjoy an exceptional home, spectacular views, and two distinguished golf courses without the customary membership waitlist.

3410 Runaway CT, 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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