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

12324 Wisteria DR, Naples
$1,750,000
4 Beds ⋅ 3.5 Baths ⋅ 226039431 MLS
Refined luxury and tranquil lake views come together in this beautifully appointed Naples residence offering four bedrooms, three full baths, one half bath, and a three-car garage. Framed by mature palms and lush tropical landscaping, the home welcomes you with a paver driveway, distinctive architectural detailing, and an impressive double-door entry. Soaring ceilings, intricate tray and coffered designs, crown molding, and abundant natural light create an elegant yet inviting atmosphere. The open living area flows seamlessly into a stunning kitchen featuring white cabinetry, an expansive island with seating, stainless steel appliances, a decorative range hood, and an illuminated tile backsplash. Architectural wall molding enhances the formal dining room, while the bright breakfast area offers picturesque views of the pool and lake. The spacious primary suite provides a serene escape with a bay-window sitting area, plantation shutters, decorative wall trim, and a tray ceiling. The luxurious primary bath features separate vanities, a soaking tub, and an expansive glass-enclosed shower surrounded by elegant marble-look tile. Additional bedrooms provide welcoming accommodations, while a dedicated workspace with built-in cabinetry adds everyday convenience. An exceptional outdoor retreat awaits on the expansive screened lanai, where a sparkling pool with a sun shelf and raised spa overlooks the peaceful lake. A richly finished wood ceiling crowns the covered entertaining area, complemented by an outdoor kitchen featuring a built-in grill, stainless steel hood, beverage refrigeration, and a striking blue tile backsplash. Generous spaces for dining and lounging create an ideal setting for entertaining or simply enjoying the waterfront surroundings. A well-appointed laundry room and extensive storage cabinetry in the three-car garage complete this sophisticated Florida residence.

12324 Wisteria DR, Naples

3840 CRAYTON RD, Naples
$7,095,000
5 Beds ⋅ 7.5 Baths ⋅ 226039482 MLS
One or more photo(s) has been virtually staged, AI generated or rendered. Introducing a remarkable, classic contemporary residence in the heart of Park Shore, crafted by the esteemed team of JMDG Architecture, the reputable interior design firm Clive Daniel Home, and luxury builder Asta Homes. Perfectly located just minutes from Naples’ finest shopping, dining, and beaches, this 5-bedroom plus office estate offers exceptional design, premium craftsmanship, and elevated modern living. The thoughtful floor plan provides ultimate convenience with the primary suite, a guest bedroom, and a private office all located on the first floor. Upstairs, discover three additional en-suite guest bedrooms and a massive loft/second living room, creating ideal separation and comfort for family and guests. With 8 total bathrooms, the home ensures effortless privacy and accommodation for all. The interior showcases a refined coastal modern aesthetic with wide-plank white oak floors, Elegante custom cabinetry, and distinctive architectural ceiling elements adding depth and style throughout. The gourmet kitchen is a standout, featuring high-end appliances, a spacious walk-in pantry, ample storage, a built-in coffee maker, and abundant natural light, creating a perfect blend of functionality and luxury. A dramatic pivot front door welcomes you into the open-concept living area, anchored by a sleek vapor fireplace. Built to an impressive 11 ft elevation, the home offers added peace of mind with enhanced flood protection. Modern conveniences include a Lutron lighting system, Sonos speakers throughout the main areas, and a buried propane tank, discretely integrated into the property. Designed for premier indoor/outdoor living, the home boasts an expansive covered outdoor living area complete with a full outdoor kitchen, fireplace, and a convenient pool bath, providing an ideal setting for year-round entertaining. A 3-car garage offers generous space for vehicles, storage, and coastal living essentials. Scheduled for completion in February, this exceptional Park Shore residence combines world-class design, superior construction, and an unbeatable Naples location.

3840 CRAYTON RD, Naples

1260 12th AVE N, Naples
$1,595,000
3 Beds ⋅ 2 Baths ⋅ 226039276 MLS
The quintessential Lake Park cottage—beautifully reimagined and move-in ready. Rebuilt in 2009 with only three original walls remaining, this home blends classic cottage charm with modern living. The comprehensive transformation included a new roofline with handcrafted trusses built on-site, creating 15-foot ceilings throughout the living areas and 9-foot ceilings in the bedrooms. Additional improvements included durable concrete siding for long-lasting protection, reconfigured window placements with impact-glass windows, a new garage, an additional primary suite with a luxurious bath, and redesigned landscaping in the front and back. Electrical and plumbing systems were replaced, along with lighting and fixtures, completing the extensive rebuild and creating a home entirely different from the original. Hickory floors and a cypress tongue-and-groove ceiling lend warmth and character. French doors line the entrance to the spacious, modern lanai, added just two years ago—a beautiful setting for relaxing and entertaining overlooking a lovely garden graced by a beautiful sea grape tree and an ancient oak. The backyard also offers plenty of room to add a pool. Set in the heart of the highly sought-after Lake Park neighborhood, this home places you at the center of everything that makes Naples so special. Naples’ pristine beaches are just a 10-minute bike ride or a five-minute golf cart ride away. From the celebrated shopping and dining of Fifth Avenue South and Third Street South to Baker Park, the Gordon River Greenway, Gulfshore Playhouse, and the charming shops and restaurants of the Naples Design District, you’re surrounded by the best of the coveted Naples lifestyle.

1260 12th AVE N, Naples

12065 Datura PL, Naples
$2,250,000
4 Beds ⋅ 4.5 Baths ⋅ 226033791 MLS
EXCEPTIONAL LAKEFRONT LUXURY, BREATHTAKING SUNSETS & DESIGNER FURNISHINGS IN VALENCIA TRAILS! Welcome to 12065 Datura Place, an extraordinary opportunity to own the largest Captiva model in Valencia Trails, perfectly positioned on one of the community's most desirable lakefront homesites. Boasting spectacular long lake views, exceptional privacy with no homes directly behind you, and breathtaking sunsets every evening, this residence offers a truly special setting that sets it apart from the rest. Offered beautifully furnished with exquisite, high-end furnishings, this exceptional residence features 4 spacious bedrooms, a den, 4 full bathrooms, and 1 half bath. Sophisticated design, timeless elegance, and impeccable attention to detail are evident throughout. Custom built-ins, refined finishes, and thoughtfully curated furnishings create an atmosphere of understated luxury, while the expansive floor plan offers an effortless flow between elegant entertaining spaces and comfortable everyday living. Completely move-in ready, this home allows you to begin enjoying the Naples lifestyle from the moment you arrive. Step outside to your own private lakefront retreat, where an extended lanai, sparkling swimming pool, and custom outdoor kitchen provide the ultimate setting for year-round Florida living. Whether hosting friends for dinner, relaxing poolside, or enjoying a peaceful evening overlooking the water, this exceptional outdoor space was designed to capture the beauty of its surroundings. The sweeping long lake views, remarkable privacy, and spectacular nightly sunsets create an experience that few homes can offer. Located within Valencia Trails, one of Naples' premier 55+ resort-style communities, residents enjoy an impressive array of amenities, including a magnificent clubhouse, resort-style pools, fitness center, tennis, pickleball, bocce, on-site dining, walking trails, and an active social calendar. What truly sets this home apart is its rare combination of a premier lakefront homesite, breathtaking sunset views, exceptional privacy, luxurious designer furnishings, and beautifully designed indoor-outdoor living spaces. Every detail has been thoughtfully considered to create a residence that is both sophisticated and welcoming. An exceptional home. An extraordinary setting. A lifestyle second to none.

12065 Datura PL, Naples

13567 Collier BLVD, Naples
$3,124,999
4 Beds ⋅ 3 Baths ⋅ 226038982 MLS
Exceptional craftsmanship, privacy, and sophisticated design define this stunning 2024-built estate situated on 2.37 acres in Golden Gate Estates. Offering 3,219 square feet of beautifully appointed living space, this impressive residence features 4 bedrooms, 3 bathrooms, a private pool and spa, and a spacious 3-car garage. Constructed with poured concrete rather than traditional concrete block, this home showcases quality construction and meticulous attention to detail. Impact resistant windows and doors, hardwood flooring throughout, custom lighting, and extensive built-ins enhance the home's refined interior. The luxurious primary suite features an expansive walk-in closet with custom built-ins, while an additional bedroom offers custom cabinetry. The beautifully designed den includes a custom double-sided built-in desk, creating an elegant and functional home office. A striking built-in wine cellar with capacity for more than 200 bottles provides a dramatic focal point and exceptional feature for entertaining. Designed for the ultimate Florida lifestyle, the outdoor living area is equally impressive. The private pool and spa are complemented by custom planters with integrated water features, a sun deck, and thoughtfully designed landscaping. A fully equipped outdoor kitchen provides the perfect setting for entertaining, dining and relaxing year round. The paved driveway enhances the home's curb appeal, while the 3 car garage features a dedicated mini-split A/C system, providing additional comfort and versatility. Set on an expansive 2.37 acre homesite, this distinctive Golden Gate Estates residence delivers a rare combination of privacy, acreage, substantial poured-concrete construction, custom finishes, and resort-inspired outdoor living - all in Naples!

13567 Collier BLVD, Naples

5550 Heron Point DR Unit 1501, Naples
$1,895,000
3 Beds ⋅ 2 Baths ⋅ 226037322 MLS ⋅ St Nicole BLDG.
Sweeping Gulf views and vibrant sunsets define this beautifully renovated residence on the 15th floor of St. Nicole in Pelican Bay. Positioned along the south-end boardwalk, St. Nicole enjoys a prime coastal setting with convenient access to Pelican Bay’s private beaches. Ideally situated in the center stack, the three-bedroom, two-bath condo offers 1,905 sq ft of thoughtfully redesigned living space with exceptional natural light and privacy. Large-format natural shellstone flooring extends throughout the interiors and onto two expansive lanais. The open kitchen features raised ceilings, quartz countertops, a glass backsplash and KitchenAid stainless steel appliances. A private primary suite offers its own screened lanai, custom walk-in closets, dual vanities and a spacious walk-in shower. Two guest bedrooms feature custom closet storage and share a full bath, with one currently arranged as a private office and sitting area. Impact-resistant windows and sliders, generous built-in storage and an oversized storage closet just outside the residence complete the home. St. Nicole amenities include two guest suites, a sunny south-facing pool and spa, fitness center, social spaces and on-site management. Pelican Bay offers an exceptional coastal lifestyle, with nearly three miles of pristine Gulf shoreline, private beach access and attentive chair and umbrella service. Steps from St. Nicole, an open-air tram winds through the mangrove preserve to beachfront dining at Marker 36 and Sandbar. Tennis, pickleball, sailing and kayaking complement a community fitness center, wellness studio and scenic walking and biking paths. Enjoy nearby destinations—Waterside Shops, Artis–Naples, fine dining, and upscale shopping—with quick access to all Naples offers.

5550 Heron Point DR Unit 1501, Naples

5835 Hidden Oaks LN, Naples
$1,499,999
4 Beds ⋅ 2.5 Baths ⋅ 226039527 MLS
Rare 2.25-Acre Estate Opportunity in Desirable Oakes Estates – North Naples! Discover the exceptional opportunity to build your dream estate on 2.25 acres of highly desirable land in Oakes Estates, one of North Naples’ sought-after communities for those who value space, privacy, and a peaceful setting. Surrounded by beautiful pine trees and a natural tree line, this unique property offers a tranquil atmosphere with little to no street noise, creating the perfect backdrop for your own private Florida retreat. The generous acreage provides endless possibilities to design and build a custom luxury residence, complete with the outdoor living spaces, pool, guest accommodations, and additional features you have always envisioned. The property is gated, offering an added sense of privacy and exclusivity, while the mature pine-filled landscape creates a natural buffer from the surrounding area. The existing home on the property has never flooded, providing additional peace of mind. A pool house is also situated on the land and is being offered in AS-IS condition; Opportunities to secure 2.25 acres in Oakes Estates are increasingly special for buyers seeking the freedom to create a custom home without sacrificing privacy or convenience. Enjoy the feeling of a private estate setting while remaining within reach of North Naples’ shopping, dining, beaches, and everyday amenities. Whether you envision a secluded luxury retreat, a sprawling family estate, or a custom-designed home surrounded by nature, this property offers an outstanding canvas to bring your vision to life. Bring your builder and discover the possibilities of this exceptional Oakes Estates property! DO NOT ENTER PROPERTY WITHOUT APPOINTMENT.

5835 Hidden Oaks LN, Naples

962 8th AVE S, Naples
$1,899,000
2 Beds ⋅ 2 Baths ⋅ 2026023621 MLS ⋅ Sandpiper Cove BLDG.
Experience the privacy of single family style living in this exquisitely renovated two story residence in the heart of Olde Naples. One of just four residences in an intimate boutique building, this exceptional home offers a private retreat just steps from the shopping and dining of 5th Avenue South and 3rd Street South and Naples' famous sugar-sand beaches. Soaring vaulted ceilings, a custom fireplace, and elegant linen drapery enhance the light-filled great room, which opens seamlessly to a lanai for effortless indoor-outdoor living. The chef's kitchen is an entertainer's dream, featuring an oversized Taj Mahal quartzite island, pull-out pantry, and thoughtfully designed cabinetry for all your entertaining essentials. A main level guest suite doubles as a second primary, offering comfort and privacy for visitors. A bespoke oak staircase with custom lighting leads to the spacious primary retreat, complete with a skylight, fireplace, and walk-in closet with custom built-in organization. The spa inspired bath features a soaking tub, beautifully tiled shower, and defogging mirrors. Upstairs, a versatile media room/loft, office area with wet bar, and balcony overlooking the pool provide additional spaces to relax and entertain. A rare Olde Naples luxury, the full size walk-in laundry room includes a utility sink, cabinetry, and dedicated folding area. Completely remodeled in 2026, this move-in-ready residence offers all-new impact windows and doors, 2026 HVAC, 2026 tankless water heater, brand-new appliances, and custom window treatments throughout. Having remained high and dry through every hurricane, this home offers peace of mind for full-time and seasonal residents alike. An attached covered carport with direct entry and the option to convert to a garage adds another highly coveted Olde Naples convenience. Luxury, privacy, and an unbeatable location come together in this exceptional coastal retreat. Schedule your private showing today and discover the best of Olde Naples living!

962 8th AVE S, Naples

634 19th ST SW, Naples
$3,347,800
5 Beds ⋅ 5.5 Baths ⋅ 226039488 MLS
Luxury Estate Living on 2.27 Acres in Golden Gate Estates Experience the perfect blend of luxury, privacy, and functionality in this exceptional custom estate nestled on 2.27 acres of 100% uplands in the highly desirable Golden Gate Estates. Offering over 4,600 square feet of air-conditioned living space, this thoughtfully designed home features 5 spacious bedrooms, a private den, 5 full bathrooms, and 1 half bath, making it ideal for families, entertaining, or multigenerational living. From the moment you step inside, you'll appreciate the craftsmanship and attention to detail. The chef's kitchen is a true showpiece, featuring premium ZLINE appliances, a KitchenAid refrigerator, an abundance of floor-to-ceiling custom cabinetry, and an expansive walk-in pantry complete with additional built-in cabinetry for exceptional storage and organization. A fully equipped secondary kitchen provides the perfect space for guests, extended family, or effortless entertaining. Each of the five bedrooms offers the comfort and privacy of its own en-suite bathroom, while every bathroom showcases elegant floating vanities with integrated LED accent lighting, creating a sophisticated spa-like atmosphere throughout the home. Designed with convenience in mind, the oversized laundry room includes dual washers and dryers, extensive cabinetry, and a dedicated dog wash station—perfect for busy households and pet lovers alike. Step outside to your own private resort where a saltwater pool, heated spa, and expansive outdoor living area create the ultimate setting for relaxation and entertaining. The fully equipped outdoor kitchen features premium Napoleon and ZLINE appliances, allowing you to enjoy Southwest Florida's year-round outdoor lifestyle. Additional premium features include a 4-car garage with epoxy floors, a 500-gallon buried propane tank, and a 26kW Generac whole-house generator, providing peace of mind and uninterrupted comfort. The property also features a paved driveway extending all the way to the rear of the property, already prepared for a future guest house, workshop, RV garage, or additional outbuilding, offering endless possibilities to customize the estate to your needs. Combining luxurious finishes, modern amenities, exceptional functionality, and the privacy of a fully upland homesite, this remarkable Golden Gate Estates property is a rare opportunity to own one of Naples' finest custom-built estates.

634 19th ST SW, Naples

9130 Limestone LN, Naples
$996,000
2 Beds ⋅ 2 Baths ⋅ 226038148 MLS
EXQUISITE WATER, GOLF COURSE & PRESERVE VIEWS! Experience the beauty and tranquility of one of The Quarry’s most desirable settings, where a picturesque water view featuring natural rock accents, sweeping green fairways, and a lush preserve beyond create a captivating backdrop for everyday living. With coveted eastern exposure across the rear of the home, enjoy peaceful mornings on the lanai with coffee and spectacular sunrises over the water. From the front of the home, take in beautiful Naples sunsets, offering the best of both morning and evening scenery. This inviting residence features 2 bedrooms plus a den, easily accommodating a 3rd bedroom, and 2 full baths. Sleek tile flooring flows throughout the main living areas, complemented by warm hardwood floors in the bedrooms and den. The chef-inspired kitchen pairs crisp white shaker cabinetry with striking black quartz countertops for a timeless, sophisticated aesthetic. Thoughtful upgrades enhance both comfort and functionality, including plantation shutters, Silhouette window shades, electric Storm Smart hurricane screens, and custom closet organization systems throughout. Additional features include a picture window on the lanai, plus a heated saltwater pool with solar panels for added efficiency and year-round enjoyment. Beyond the home, discover the exceptional lifestyle of The Quarry, a gated, amenity-rich community encompassing more than 500 acres of navigable lakes. Enjoy boating, kayaking, paddleboarding, jet skiing, and fishing, or unwind at the Beach Club with its resort-style and lap pools, spa, tennis, pickleball, bocce, dining, tiki bar, modern fitness center, and vibrant calendar of social activities. Optional golf membership is available at The Quarry Golf Lodge, home to an acclaimed 18-hole Hurdzan-Fry-designed course. With its enchanting rock-accented water views, eastern rear exposure, sweeping golf course scenery, and lush preserve backdrop, this exceptional property offers a rare opportunity to enjoy peaceful, picturesque living in one of Naples’ most distinctive lakefront communities.

9130 Limestone LN, Naples

Start Your Search

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.

How much is your home worth?

Get instant property value now!