Explore Homes for Sale in Olde Cypress, Naples, FL
Map Search for Olde Cypress, Naples, FL Homes for Sale

Homes for Sale in Olde Cypress, Naples, FL: Your Exclusive Golf Course Sanctuary

  Advanced Search   Market Reports   Home Value   Connect

Olde Cypress, Naples, FL, presents an exceptional opportunity for discerning buyers seeking homes for sale within a vibrant, private golf course community. Discover an array of luxurious residences, from elegant single-family homes to spacious villas, all offering unparalleled access to the P.B. Dye-designed golf course and resort-style amenities. As part of the desirable North Naples area, Olde Cypress offers a coveted lifestyle, combining championship golf, fine dining, and proximity to stunning Gulf beaches, making it an ideal destination for those pursuing an elevated Southwest Florida living experience. Broker Brothers proudly showcases these exquisite properties.

< Search all Homes for Sale in Naples, FL

Search Olde Cypress, Naples, FL by Lifestyle
Search Olde Cypress, Naples, FL by Price
Search Olde Cypress, Naples, FL by Bedrooms
Search Olde Cypress, Naples, FL by Bathrooms

Discovering Olde Cypress: Premier Homes for Sale in Naples, FL

For those exploring the refined real estate landscape of Southwest Florida, the availability of homes for sale in Olde Cypress, Naples, FL, represents an unparalleled opportunity. This private, gated community embodies the essence of luxury golf course living, perfectly situated in the desirable North Naples area. The allure of Olde Cypress extends beyond its meticulously maintained grounds and stunning residences, offering a lifestyle rich in amenities and natural beauty.

An Unrivaled Lifestyle and Amenities

Life in Olde Cypress revolves around its exceptional amenities. Residents enjoy exclusive access to the Olde Cypress Club, which serves as the social heart of the community. This includes fine and casual dining options, a state-of-the-art fitness center, a resort-style swimming pool, and vibrant social activities. The transition from a leisurely morning swim to an afternoon on the greens is seamless, defining the ease of living here.

Championship Golf Course Homes

Central to the appeal of Olde Cypress homes for sale is the championship P.B. Dye-designed golf course. This challenging yet picturesque course winds through the community, offering breathtaking views from many properties. Golf enthusiasts will find themselves immersed in a world-class experience, with opportunities for both competitive play and social rounds. The presence of such a distinguished course significantly enhances the value and desirability of Olde Cypress real estate.

Exploring the Types of Homes for Sale in Olde Cypress

The architectural diversity within Olde Cypress ensures that there are homes for sale to suit a wide range of preferences and needs. From elegant villas perfect for seasonal residents to expansive estate homes designed for year-round luxury, the options are plentiful and impeccably maintained.

Exquisite Single-Family Residences

Many of the homes for sale in Olde Cypress are distinguished single-family residences. These properties often feature spacious layouts, gourmet kitchens, private lanais with pools, and stunning views of the golf course or serene preserves. They represent the pinnacle of comfortable and elegant living, meticulously crafted with high-end finishes and thoughtful designs.

Luxurious Villas and Estate Homes

In addition to traditional single-family homes, Olde Cypress also offers luxurious villas and grand estate homes. The villas provide a lower-maintenance option without sacrificing luxury or access to community amenities, ideal for those seeking a lock-and-leave lifestyle. Estate homes, on the other hand, offer expansive living spaces, often including multiple bedrooms, private studies, and elaborate outdoor entertainment areas, catering to those who desire ultimate privacy and grandeur within a vibrant community.

Why Choose Olde Cypress for Your Next Home

Selecting one of the homes for sale in Olde Cypress means investing in a lifestyle and location that are highly sought after in the Naples real estate market. The community's blend of exclusivity, natural beauty, and strategic location makes it an intelligent choice for discerning buyers.

Community Exclusivity and Prime Location

Olde Cypress boasts a prime North Naples location, providing residents with easy access to pristine Gulf beaches, upscale shopping destinations like Mercato and Waterside Shops, and a plethora of fine dining establishments. Yet, within its gates, a sense of tranquil exclusivity prevails, offering a perfect balance of convenience and privacy. The proximity to I-75 also ensures straightforward travel to Southwest Florida International Airport (RSW) and other regional attractions.

Market Trends and Investment Potential

The real estate market in Olde Cypress, Naples, FL, consistently demonstrates strong performance, reflecting the enduring appeal of golf course communities in affluent areas. Properties here tend to hold their value well, offering robust investment potential for future homeowners. The demand for homes for sale in such a desirable location, coupled with the community's established reputation, makes Olde Cypress a sound long-term investment.

Finding Your Dream Home with Broker Brothers

As experts in the Naples real estate market, Broker Brothers is dedicated to helping you navigate the selection of homes for sale in Olde Cypress. Our in-depth local knowledge and commitment to client satisfaction ensure a seamless and enjoyable home-buying journey. Discover the exceptional beauty and luxury that await you in Olde Cypress, Naples, FL.

Newest Homes for Sale in Olde Cypress, Naples, FL

$749,900
3 Beds ⋅ 2 Baths ⋅ 226024092 MLS ⋅ Olde Cypress BLDG.
This charming 3Br/2Ba detached villa offers the perfect blend of comfort and privacy situated on a private corner lot. This home features a spacious open-concept living and dining area. A bright kitchen with Raised panel Cherry cabinets, ample storage, offers granite countertops, tile backsplash, kitchen island w/ cook-top, wall oven & microwave, and breakfast bar. Great room features plantation shutters, tray ceiling w/ recessed lighting and French doors to the lanai pool area. The master bedroom offers a private door to a side patio, his & her walk-in closets, tray ceiling, walk-in shower, dual sinks and ladies seated vanity. Other features: Additional Guest room and second full bath with tub and shower. Neutral tile flooring and wood floors throughout main living area, private pool w/ privacy wall, expansive yard, volume ceilings, & recessed lighting. Olde Cypress is a low-density gated community with 550 single family homes, located in North Naples, the Social Membership allows residents to use the clubhouse facilities which include club activities, fine & casual dining, tennis, pickleball, swimming pool, fitness and meeting rooms. Residences of the community may enhance their privileges by upgrading to a Golf Membership on the prestigious P.B Dye 18-hole designed course. New renovated Clubhouse brings Olde Cypress to a class of it own. Olde Cypress is located just off I-75, allowing easy access to Fort Myers airport, numerous restaurants, beaches and shopping.

3155 Santorini Ct, Naples
$1,995,000
3 Beds ⋅ 3 Baths ⋅ 226019476 MLS ⋅ Olde Cypress BLDG.
Set against a picturesque golf course and lake backdrop with no homes in sight, this beautifully upgraded residence offers refined living in the sought-after community of Olde Cypress. Spanning approximately 2,800 square feet, the home features three bedrooms, a private study, and three full baths, thoughtfully designed for both everyday comfort and effortless entertaining. A grand interior unfolds with soaring 12- to 14-foot ceilings, expansive 9-foot sliders, and solid core 8-foot doors. Recent enhancements elevate the home with a new hurricane-rated front door, designer lighting and fixtures, architectural wood beam accents, luxury wood-look LVP flooring throughout the main living areas, and upgraded carpeting in the bedrooms. Crown molding and plantation shutters add timeless elegance, while a restored gas fireplace creates a warm focal point. The redesigned chef’s kitchen is a standout, featuring a brand-new LG stainless steel appliance package, double ovens with convection cooking, and a gas cooktop powered by a 250-gallon tank that also services the fireplace. Quartz countertops, custom cabinetry, a marble backsplash, and an oversized stainless-steel sink complete the space, while a large island with bar seating for four makes it ideal for gathering. The kitchen flows seamlessly into the family room, enhancing functionality and connection. The spacious primary suite offers tranquil golf course views, dual walk-in closets, and a well-appointed bath. All bathrooms have been tastefully updated with renovated vanities, granite countertops, and new fixtures for a clean, modern finish. Outdoor living is equally impressive, featuring a deep covered lanai with soaring ceilings alongside a sun-filled travertine pool deck. The pool has been fully upgraded with a new pebble finish, updated waterline tile, LED lighting, and brand-new equipment including pumps and a heater. A picture-frame enclosure has been re-screened and painted to maximize the stunning views. Additional upgrades include fresh exterior paint, sealed pavers, and refreshed landscaping. A newer roof (2021) and oversized garage with a dedicated golf cart bay add convenience. Located within Olde Cypress, residents enjoy a vibrant and active lifestyle with a mandatory social membership that provides access to a full suite of amenities. The community features a dynamic year-round social calendar, formal and informal dining with no food and beverage minimums, and exceptional recreational offerings including tennis, pickleball, bocce, a lap pool, and a state-of-the-art fitness center. Championship golf by P.B. Dye is optional, with both full and associate memberships available, offering flexibility to suit a variety of lifestyles. This premier North Naples community delivers the perfect balance of luxury, leisure, and convenience.

3105 Terramar Dr, Naples
$3,390,000
4 Beds ⋅ 4.5 Baths ⋅ 226015132 MLS ⋅ Olde Cypress BLDG.
One or more photo(s) has been virtually staged, AI generated or rendered. Welcome to an amazing opportunity in Da Vinci Estates at Olde Cypress—an exclusive DOUBLE-GATED community known for estate-sized homes and unparalleled privacy. This property has LAKE VIEWS, a RARE FIVE-CAR GARAGE and a GUEST HOUSE. Major 2025 upgrades include: NEW ROOF, GUTTERS, FULL EXTERIOR PAINT, AND HVAC. Designed for both luxury living and entertaining, the home features a chef’s kitchen with a Viking gas range, Bosch dishwasher and Fisher & Paykel double oven. Expansive pocketing sliding glass doors seamlessly retract into the walls, creating a complete indoor-outdoor living experience that leads to the HEATED POOL and GROTTO SPA. The main floor features a full East-Wing primary suite that has a cocktail/coffee bar, double vanities, free-standing bathtub, private shower room, oversized walk-in closet, and a sitting room that leads to a PRIVATE GARAGE ENTRY. The main floor also features an office, 2 living rooms, formal dining, laundry room, half bathroom, gourmet kitchen and 2 bedrooms with a jack & jill bathroom. The second-floor entertainment level has a MOVIE THEATER AND BILLIARDS ROOM with a half bath. The seperate guest house or in-law suite is 1 bed/1 bath with a wet bar and has beautiful lake views with sliding doors leading to the pool area. Located in a premier North Naples golf community with a P.B. Dye championship course, FULL and ASSOCIATE GOLF MEMBERSHIPS AVAILABLE, and a newly completed $17M CLUBHOUSE TRANSFORMATION (NO ASSESSMENTS & NO FOOD/BEVERAGE MIN).

3027 Mona Lisa Blvd, Naples
$1,630,000
4 Beds ⋅ 2.5 Baths ⋅ 226003848 MLS ⋅ Olde Cypress BLDG.
Welcome to effortless Florida living in the prestigious Olde Cypress community, home to a celebrated P.B.Dye–designed golf course. This beautifully appointed fully turnkey Ruffino II residence allows you to simply arrive, unwind, and begin enjoying the lifestyle you’ve been waiting for—just bring your suitcase. Designed with both elegance and peace of mind, the light-filled interior features custom crown molding, plantation shutters throughout, and hurricane impact windows and doors, providing comfort, security, and energy efficiency year-round. The open-concept living space flows seamlessly into a stylish kitchen with stainless steel appliances, granite countertops, and solid wood cabinetry—ideal for entertaining or relaxed evenings at home. A private den offers flexible space for work or leisure, while the inviting bedrooms serve as peaceful retreats. The home also includes a spacious 3-car garage equipped with a storage lift, offering exceptional functionality for vehicles, bikes, golf gear, and seasonal storage. Step outside to your private outdoor oasis. The oversized lanai is thoughtfully designed for year-round enjoyment and features an upgraded Super Screen enclosure, allowing expansive views and refreshing breezes while keeping comfort top of mind. Complete with an outdoor kitchen, sparkling pool and spa, upgraded lighting, and a calming water feature, this space is perfect for morning coffee, afternoon relaxation, or sunset gatherings. Olde Cypress offers a vibrant social lifestyle with a mandatory social membership and optional golf memberships. Golf carts are welcome throughout the community, making it easy to cruise to the clubhouse, meet neighbors, or enjoy the laid-back Florida lifestyle. Conveniently located just minutes from I-75 and within 30 minutes of RSW, this home offers the ideal blend of accessibility and escape. Relaxed. Refined. Secure. Ready for you.

7352 Lantana Way, Naples
Start Your Search